4-Chlorobenzoyl chloride → HCID 20298377, compound

HRID 1389224Notes

Reaction equation

HRID 1389224 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([NH:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>C1C=CC=CC=1>[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([N:7]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]2[CH:5]=[CH:6][C:1]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:2][CH:3]=2)=[O:37])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 20298420HCID 20298420, compound

Product 1

HCID 20298377HCID 20298377, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Analogously to Example 47b), 10.0 g of ethyl 4-(biphenyl-4-yl)aminobutyrate and 4.6 g of ethyldiisopropylamine in 70 ml of benzene are reacted with 6.2 g of p-chlorobenzoyl chloride to obtain 9.4 g (62.9% of theory) of ethyl 4-[p-chloro-N-(biphenyl-4-yl)benzamido]butyrate as a viscous non-distillable oil. Saponification of this ester, analogously to Example 47c), yields 7.0 g (79.7% of theory) of 4-[p-chloro-N-(biphenyl-4-yl)-benzamido]butyric acid, MP 192° to 194°.

Sources & evidence

ORD record
ord-0dccbbab2ab640ca87bcbb0f707d4f8d
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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