CH633531A5 - Process for the preparation of substituted N,N-dialkylthiocarbamic acid S-benzyl esters - Google Patents

Process for the preparation of substituted N,N-dialkylthiocarbamic acid S-benzyl esters Download PDF

Info

Publication number: CH633531A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; chloride; benzyl; thiocarbamic acid; reaction
Prior art date: 1977-10-03

Application number

CH1202477A

Other languages

German (de)

English (en)

Inventor

Barna Dipl Chem Dr Bordas

Karoly Dipl Chem Dr Balogh

Gusztav Gal

Jozsefne Dipl Chem Dr Grega

Gyoergy Dipl Chem Dr Matolcsy

Sandor Dipl Chem Nagy

Zoltan Dipl Ing Dr Pinter

Nandor Vago

Original Assignee

Eszakmagyar Vegyimuevek

Noevenyvedelmi Kutato Intezet

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.)

1977-10-05

Filing date

1977-10-03

Publication date

1982-12-15

1977-10-03 Application filed by Eszakmagyar Vegyimuevek, Noevenyvedelmi Kutato Intezet filed Critical Eszakmagyar Vegyimuevek

1982-12-15 Publication of CH633531A5 publication Critical patent/CH633531A5/de

Links

238000000034 method Methods 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 3
239000002253 acid Substances 0.000 title description 4
238000006243 chemical reaction Methods 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 8
229940073608 benzyl chloride Drugs 0.000 claims description 7
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
-1 polymethylene group Polymers 0.000 claims description 2
229910001507 metal halide Inorganic materials 0.000 claims 1
150000005309 metal halides Chemical class 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 10
238000009835 boiling Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
LOFZYSZWOLKUGE-UHFFFAOYSA-N s-benzyl carbamothioate Chemical compound NC(=O)SCC1=CC=CC=C1 LOFZYSZWOLKUGE-UHFFFAOYSA-N 0.000 description 6
150000005524 benzylchlorides Chemical class 0.000 description 5
238000004821 distillation Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
229960003750 ethyl chloride Drugs 0.000 description 4
239000007858 starting material Substances 0.000 description 4
235000005074 zinc chloride Nutrition 0.000 description 4
239000011592 zinc chloride Substances 0.000 description 4
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 3
QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 3
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical class SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
230000007797 corrosion Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 2
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 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 2
125000005265 dialkylamine group Chemical group 0.000 description 2
UAGGVDVXSRGPRP-UHFFFAOYSA-N diethylcarbamothioic s-acid Chemical compound CCN(CC)C(S)=O UAGGVDVXSRGPRP-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
229910001510 metal chloride Inorganic materials 0.000 description 2
239000011814 protection agent Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
UJXIOVIFPTXDHU-UHFFFAOYSA-N 2-phenylethanethioyl chloride Chemical compound ClC(=S)CC1=CC=CC=C1 UJXIOVIFPTXDHU-UHFFFAOYSA-N 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
229910001626 barium chloride Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000005131 dialkylammonium group Chemical group 0.000 description 1
NCPDPTXSMJDCIH-UHFFFAOYSA-N dipropylcarbamothioic s-acid Chemical compound CCCN(C(S)=O)CCC NCPDPTXSMJDCIH-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
BKXRWLMGHBHCFY-UHFFFAOYSA-N s-benzyl n,n-diethylcarbamothioate Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1 BKXRWLMGHBHCFY-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
SNCHEDBJOUWPMJ-UHFFFAOYSA-M sodium;phenylmethanethiolate Chemical compound [Na+].[S-]CC1=CC=CC=C1 SNCHEDBJOUWPMJ-UHFFFAOYSA-M 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003560 thiocarbamic acids Chemical class 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid

Landscapes

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

CH1202477A 1977-10-05 1977-10-03 Process for the preparation of substituted N,N-dialkylthiocarbamic acid S-benzyl esters CH633531A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU78250A LU78250A1 (fr)	1977-10-05	1977-10-05

Publications (1)

Publication Number	Publication Date
CH633531A5 true CH633531A5 (en)	1982-12-15

Family

ID=19728724

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1202477A CH633531A5 (en)	1977-10-05	1977-10-03	Process for the preparation of substituted N,N-dialkylthiocarbamic acid S-benzyl esters

Country Status (8)

Country	Link
AT (1)	AT351560B (fr)
BE (1)	BE859599A (fr)
CH (1)	CH633531A5 (fr)
DE (1)	DE2745009A1 (fr)
FR (1)	FR2405933A1 (fr)
GB (1)	GB1566474A (fr)
LU (1)	LU78250A1 (fr)
NL (1)	NL7711165A (fr)

1977
- 1977-10-03 CH CH1202477A patent/CH633531A5/de not_active IP Right Cessation
- 1977-10-04 AT AT704677A patent/AT351560B/de not_active IP Right Cessation
- 1977-10-05 LU LU78250A patent/LU78250A1/xx unknown
- 1977-10-06 GB GB4167977A patent/GB1566474A/en not_active Expired
- 1977-10-06 DE DE19772745009 patent/DE2745009A1/de not_active Withdrawn
- 1977-10-11 BE BE181639A patent/BE859599A/fr not_active IP Right Cessation
- 1977-10-11 NL NL7711165A patent/NL7711165A/xx not_active Application Discontinuation
- 1977-10-12 FR FR7730668A patent/FR2405933A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
AT351560B (de)	1979-08-10
LU78250A1 (fr)	1978-01-26
NL7711165A (nl)	1979-04-17
FR2405933A1 (fr)	1979-05-11
GB1566474A (en)	1980-04-30
DE2745009A1 (de)	1979-04-12
ATA704677A (de)	1979-01-15
BE859599A (fr)	1978-02-01

Legal Events

Date	Code	Title	Description
1987-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

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