Dimethyl Sulfoxide → HCID 20292164, compound

HRID 1389206Notes

Reaction equation

HRID 1389206 reaction equation
[CH:1]([NH:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([O:42][CH3:43])=[C:37]([CH:41]=1)[C:38](Cl)=[O:39].CS(C)=O>C1C=CC=CC=1>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([O:42][CH3:43])=[C:37]([CH:41]=1)[C:38]([N:14]([CH:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:39]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 20292150HCID 20292150, compound

Product 1

HCID 20292164HCID 20292164, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Analogously to Example 19, 8.9 g of ethyl 4-benzhydrylaminobutyrate and 4.3 g of ethyl diisopropylamine are dissolved in 80 ml of benzene and reacted with a solution of 6.8 g of 5-chloro-2-methoxybenzoic acid chloride in 20 ml of benzene. As reaction product one obtains 13.8 g (99% of theory) of ethyl N-(5-chloro-2-methoxybenzoyl)-4-benzhydrylaminobutyrate as a viscous non-distillable oil. The saponification of this ester yields 11.1 g (85.6% of theory) of N-(5-chloro-2-methoxybenzoyl)-4-benzhydrylaminobutyric acid (M.P. 176° to 178°).

Sources & evidence

ORD record
ord-219b5c21e9aa4b41a8d1f75e59a0da6e
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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