Dimethyl Sulfoxide → HCID 20292210, compound

HRID 1389212Notes

Reaction equation

HRID 1389212 reaction equation
[CH:1]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([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:33](Cl)(=[O:37])/[CH:34]=[CH:35]/[CH3:36].CS(C)=O>C1C=CC=CC=1>[C:33]([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][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:37])/[CH:34]=[CH:35]/[CH3:36]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 643131trans-Crotonyl chlorideHCID 20292147HCID 20292147, compound

Product 1

HCID 20292210HCID 20292210, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Analogously to Example 19, 7 g of ethyl 5-benzhydrylaminovalerate and 3.2 g of ethyldiisopropylamine are dissolved in 100 ml of benzene and reacted with 2.6 g of crotonyl chloride. As reaction product one obtains 8.5 g of ethyl N-crotonoyl-5-benzhydrylaminovalerate as a viscous non-distillable oil. The saponification of this ester yields 6 g (76%) of N-crotonoyl-5-benzhydrylaminovaleric acid (M.P. 88° to 89°).

Sources & evidence

ORD record
ord-44f830f5e8524d478da28f8747d1af82
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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