Dimethyl Sulfoxide → HCID 20292175, compound

HRID 1389209Notes

Reaction equation

HRID 1389209 reaction equation
[CH:1]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([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:34](Cl)(=[O:38])[CH:35]([CH3:37])[CH3:36].CS(C)=O>C1C=CC=CC=1>[C:34]([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][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:38])[CH:35]([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 20292080HCID 20292080, compound

Product 1

HCID 20292175HCID 20292175, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Analogously to Example 19, 7 g of ethyl 6-benzhydrylaminocaproate and 3.1 g of ethyl diisopropylamine are dissolved in 100 ml of benzene and reacted with 2.5 g of isobutyryl chloride. As reaction product one obtains 7.8 g of ethyl N-isobutyryl-6-benzhydrylaminocaproate as a viscous non-distillable oil. The saponification of this ester yields 6.1 g (77%) of N-isobutyryl-6-benzhydrylaminocaproic acid (M.P. 106° to 107°).

Sources & evidence

ORD record
ord-13ebc2476ad74634a48b5e894e8b2000
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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