CA1088098A - Preparation d'isobutyramides - Google Patents

Preparation d'isobutyramides

Info

Publication number: CA1088098A
Authority: CA; Canada
Prior art keywords: isobutyramide; formula; chlorophenoxy; cyanoethyl; sodium
Prior art date: 1976-03-17
Legal status (The legal status 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 status listed.): Expired

Application number

CA274,001A

Other languages

English (en)

Inventor

Andre Esanu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Societe dEtudes de Produits Chimiques SA

Original Assignee

Societe dEtudes de Produits Chimiques SA

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.)

1976-03-17

Filing date

1977-03-15

Publication date

1980-10-21

1976-03-17 Priority claimed from GB10643/76A external-priority patent/GB1577413A/en

1977-03-15 Application filed by Societe dEtudes de Produits Chimiques SA filed Critical Societe dEtudes de Produits Chimiques SA

1980-10-21 Application granted granted Critical

1980-10-21 Publication of CA1088098A publication Critical patent/CA1088098A/fr

Status Expired legal-status Critical Current

Links

WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical class CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
229940047889 isobutyramide Drugs 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
WNWIKDZYZPGMDJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(2-cyanoethyl)-2-methylpropanamide Chemical compound N#CCCNC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 WNWIKDZYZPGMDJ-UHFFFAOYSA-N 0.000 claims description 7
VMMXVYZCORHEDE-UHFFFAOYSA-N n-(2-cyanoethyl)-2-(4-fluorophenoxy)-2-methylpropanamide Chemical compound N#CCCNC(=O)C(C)(C)OC1=CC=C(F)C=C1 VMMXVYZCORHEDE-UHFFFAOYSA-N 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical class [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 7
239000002244 precipitate Substances 0.000 claims description 6
OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 5
239000002798 polar solvent Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
-1 aminoalkyl nitrile Chemical class 0.000 claims description 4
AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
238000004821 distillation Methods 0.000 claims description 4
DJJWGPHTOAHIIF-UHFFFAOYSA-N n-(4-chlorophenoxy)-2-methylpropanamide Chemical compound CC(C)C(=O)NOC1=CC=C(Cl)C=C1 DJJWGPHTOAHIIF-UHFFFAOYSA-N 0.000 claims description 4
239000012454 non-polar solvent Substances 0.000 claims description 4
XOCFYLSDBIPWTP-UHFFFAOYSA-N 2-methyl-n-phenoxypropanamide Chemical class CC(C)C(=O)NOC1=CC=CC=C1 XOCFYLSDBIPWTP-UHFFFAOYSA-N 0.000 claims description 3
BAZSCNDLRZMBRM-UHFFFAOYSA-N 2-(4-fluorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(F)C=C1 BAZSCNDLRZMBRM-UHFFFAOYSA-N 0.000 claims description 2
WJGMRQMOURZHLH-UHFFFAOYSA-N N-(4-fluorophenoxy)-2-methylpropanamide Chemical compound C(C(C)C)(=O)NOC1=CC=C(C=C1)F WJGMRQMOURZHLH-UHFFFAOYSA-N 0.000 claims description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
239000000126 substance Substances 0.000 claims 5
CFPLEOLETMZLIB-UHFFFAOYSA-M sodium;4-chlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C=C1 CFPLEOLETMZLIB-UHFFFAOYSA-M 0.000 claims 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 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000003472 neutralizing effect Effects 0.000 claims 1
238000010992 reflux Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 21
208000035150 Hypercholesterolemia Diseases 0.000 abstract description 2
201000005577 familial hyperlipidemia Diseases 0.000 abstract description 2
239000000047 product Substances 0.000 description 14
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
241000700159 Rattus Species 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000243 solution Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
235000012000 cholesterol Nutrition 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
VUNWOWKGBXOBGY-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl chloride Chemical compound CC(C)(Br)C(Cl)=O VUNWOWKGBXOBGY-UHFFFAOYSA-N 0.000 description 1
RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
JJUPHRIAFLAURY-UHFFFAOYSA-N 5-aminopentanenitrile Chemical compound NCCCCC#N JJUPHRIAFLAURY-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000000871 hypocholesterolemic effect Effects 0.000 description 1
230000000999 hypotriglyceridemic effect Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
231100000456 subacute toxicity Toxicity 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA274,001A 1976-03-17 1977-03-15 Preparation d'isobutyramides Expired CA1088098A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB1063576		1976-03-17
GB10635		1976-03-17
GB10643/76A GB1577413A (en)	1976-03-17	1976-03-17	Growth of crystalline material
GB10643		1976-03-17

Publications (1)

Publication Number	Publication Date
CA1088098A true CA1088098A (fr)	1980-10-21

Family

ID=26247660

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA274,001A Expired CA1088098A (fr)	1976-03-17	1977-03-15	Preparation d'isobutyramides

Country Status (1)

Country	Link
CA (1)	CA1088098A (fr)

1977
- 1977-03-15 CA CA274,001A patent/CA1088098A/fr not_active Expired

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Legal Events

Date	Code	Title	Description
1997-10-21	MKEX	Expiry