Water → 4-[(2,4-Dichlorobenzoyl)amino]-2-chlorobenzoic acid

HRID 3571

Reaction equation

HRID 3571 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)C(C)C)(C)C.[Cl:21][C:22]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=1[CH2:24]Cl.[OH2:31]>C(Cl)Cl>[Cl:21][C:22]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=1[C:24]([NH:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([Cl:1])[CH:10]=1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 171544-Amino-2-chlorobenzoic acidHCID 81531Diisopropylethylamine

Product 1

HCID 218369754-[(2,4-Dichlorobenzoyl)amino]-2-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 5.19 g of 2-chloro-4-aminobenzoic acid in 150 ml of methylene chloride is added 7.86 g of N,N-diisopropylethylamine and 12.67 g of 2,4-dichlorobenzylchloride and stirring continued for 18 hours. Water is added to the filtrate and the organic layer dried with Na2 SO4 and concentrate in vacuo to give 13.68 g of the desired product, m.p. 171°-175° C.

Workup

  1. customthe organic layer dried with Na2 SO4
  2. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1da5671a1bbe46e789d3388e15982cfa
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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