IL30639A - Preparation of acyl derivatives of urea - Google Patents

Preparation of acyl derivatives of urea

Info

Publication number: IL30639A
Authority: IL; Israel
Prior art keywords: substituted; radical; alkyl; urea; process according
Prior art date: 1967-09-15

Application number

IL30639A

Other languages

English (en)

Other versions

IL30639A0 (en

Original Assignee

Progil

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1967-09-15

Filing date

1968-08-28

Publication date

1973-06-29

1968-08-28 Application filed by Progil filed Critical Progil

1968-10-24 Publication of IL30639A0 publication Critical patent/IL30639A0/xx

1973-06-29 Publication of IL30639A publication Critical patent/IL30639A/en

Links

238000002360 preparation method Methods 0.000 title claims description 11
239000004202 carbamide Substances 0.000 title claims description 9
125000002252 acyl group Chemical group 0.000 title description 3
238000000034 method Methods 0.000 claims description 24
-1 acyl radical Chemical class 0.000 claims description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
235000013877 carbamide Nutrition 0.000 claims description 14
229910052708 sodium Inorganic materials 0.000 claims description 13
239000011734 sodium Substances 0.000 claims description 13
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 12
150000007945 N-acyl ureas Chemical class 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000003672 ureas Chemical class 0.000 claims description 12
150000001408 amides Chemical class 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000012429 reaction media Substances 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 4
150000003385 sodium Chemical class 0.000 claims description 4
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical class C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 2
239000003701 inert diluent Substances 0.000 claims 2
CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 claims 1
125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
241000196324 Embryophyta Species 0.000 description 3
238000013019 agitation Methods 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000283986 Lepus Species 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
230000002141 anti-parasite Effects 0.000 description 1
229940125687 antiparasitic agent Drugs 0.000 description 1
239000003096 antiparasitic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
JMMLZWNYIVVPOH-UHFFFAOYSA-N n-(3,4-dichlorophenyl)benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)C1=CC=CC=C1 JMMLZWNYIVVPOH-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1836—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from derivatives of carbamic acid
- C07C273/1845—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from derivatives of carbamic acid comprising the -N-C(O)-Hal moiety

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

IL30639A 1967-09-15 1968-08-28 Preparation of acyl derivatives of urea IL30639A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR121274A FR1544745A (fr)	1967-09-15	1967-09-15	Nouveau procédé de synthèse d'acyl-urées

Publications (2)

Publication Number	Publication Date
IL30639A0 IL30639A0 (en)	1968-10-24
IL30639A true IL30639A (en)	1973-06-29

Family

ID=8638472

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30639A IL30639A (en)	1967-09-15	1968-08-28	Preparation of acyl derivatives of urea

Country Status (10)

Country	Link
AT (1)	AT281857B (fr)
BE (1)	BE720868A (fr)
CH (1)	CH488668A (fr)
CS (1)	CS151479B2 (fr)
DE (1)	DE1793412C3 (fr)
ES (1)	ES358175A1 (fr)
FR (1)	FR1544745A (fr)
GB (1)	GB1228622A (fr)
IL (1)	IL30639A (fr)
NL (1)	NL6812974A (fr)

1967
- 1967-09-15 FR FR121274A patent/FR1544745A/fr not_active Expired
1968
- 1968-08-22 GB GB1228622D patent/GB1228622A/en not_active Expired
- 1968-08-28 IL IL30639A patent/IL30639A/en unknown
- 1968-09-04 CH CH1325268A patent/CH488668A/fr not_active IP Right Cessation
- 1968-09-09 AT AT877568A patent/AT281857B/de not_active IP Right Cessation
- 1968-09-11 NL NL6812974A patent/NL6812974A/xx unknown
- 1968-09-13 BE BE720868D patent/BE720868A/xx unknown
- 1968-09-13 CS CS6446A patent/CS151479B2/cs unknown
- 1968-09-13 DE DE1793412A patent/DE1793412C3/de not_active Expired
- 1968-09-14 ES ES358175A patent/ES358175A1/es not_active Expired

Also Published As

Publication number	Publication date
DE1793412B2 (de)	1973-04-05
CH488668A (fr)	1970-04-15
IL30639A0 (en)	1968-10-24
NL6812974A (fr)	1969-03-18
ES358175A1 (es)	1970-04-01
CS151479B2 (fr)	1973-10-19
GB1228622A (fr)	1971-04-15
FR1544745A (fr)	1968-11-08
BE720868A (fr)	1969-02-17
DE1793412A1 (de)	1972-04-13
DE1793412C3 (de)	1973-10-25
AT281857B (de)	1970-06-10

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