Dimethyl Sulfoxide → HCID 20292137, compound

HRID 1389202Notes

Reaction equation

HRID 1389202 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.[C:32](Cl)(=[O:34])[CH3:33].CS(C)=O>C1C=CC=CC=1>[C:32]([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:34])[CH3:33]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 20292150HCID 20292150, compound

Product 1

HCID 20292137HCID 20292137, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Analogously to Example 19, 10.8 g of ethyl 4-benzhydrylaminobutyrate and 5.2 g of ethyl diisopropylamine are dissolved in 100 ml of benzene and reacted with 3.1 g of acetyl chloride. As reaction product one obtains 11.4 g (92.5% of theory) of ethyl N-acetyl-4-benzhydrylaminobutyrate as a viscous non-distillable oil. The saponification of this ester yields 9.2 g (88% of theory) of N-acetyl-4-benzhydrylaminobutyric acid (M.P. 173° to 174°).

Sources & evidence

ORD record
ord-c612b500f2fa4bf18f5374ed7151900b
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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