4-Chlorobenzoyl chloride → HCID 20298405, compound

HRID 1389222Notes

Reaction equation

HRID 1389222 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(C(C)C)C(C)C)C.[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>C1C=CC=CC=1>[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:39])=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 20298425HCID 20298425, compound

Product 1

HCID 20298405HCID 20298405, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20.0 g of 2-aminobiphenyl, 15.3 g of ethyldiisopropylamine and 26.3 g of ethyl 6-bromocaproate are reacted, analogously to Example 47a), to obtain 36.0 g of ethyl 6-(biphenyl-2-yl)aminocaproate as a non-crystallizing oil. 18.0 g of this ester are reacted, analogously to Example 47b), with 7.5 g of ethyldiisopropylamine and 10.1 g of p-chlorobenzoyl chloride in 70 ml of benzene. The resulting reaction product is purified chromatographically over a silica gel column (eluent: methylene chloride) to obtain 11.5 g (44.2% of theory) of ethyl 6-[p-chloro-N-(biphenyl-2-yl)benzamido]caproate as a viscous non-distillable oil. Saponification of this ester yields 8.1 g (75.1% of theory) of 6-[p-chloro-N-(biphenyl-2-yl)benzamido]caproic acid, MP 93° to 95°.

Workup

  1. customThe resulting reaction product
  2. customis purified chromatographically over a silica gel column (eluent: methylene chloride)

Sources & evidence

ORD record
ord-ae5f8982d65d436486e8d722e5441dc9
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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