Carzenide → HCID 86018106, compound

HRID 883803Notes

Reaction equation

HRID 883803 reaction equation
[NH2:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:17]=1[C:18](O)=[O:19].S(Cl)([Cl:28])=O>ClC1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:17]=1[C:18]([NH:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([Cl:28])=[O:11])=[CH:12][CH:13]=1)(=[O:3])=[O:4])=[O:19]

Participants

5

Reactant 3

HCID 8739CarzenideHCID 24386Thionyl ChlorideHCID 769705-Chloro-o-anisic acid

Product 1

HCID 86018106HCID 86018106, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-aminosulfonylbenzoic acid (1 mol), 2-methoxy-5-chlorobenzoic acid (1 mol) and thionyl chloride (2.5 mol) in chlorobenzene (700 ml) was heated at 120° C. for 7-9 hours. After the reaction was complete 200 ml of the solvent was removed in vacuo. The mixture was cooled and the precipitate filtered off and washed with heptane to give the title compound, mp. 138-140° C., yield 93% of theory. 4-[[(Benzoyl)amino]sulfonyl]benzoyl chloride was prepared in a similar manner from 4-aminosulfonylbenzoic acid and benzoic acid, mp. 180-182° C., yield 96% of theory. 4-[[(2-Chlorobenzoyl)amino]sulfonyl]benzoyl chloride was prepared in a similar manner from 4-aminosulfonylbenzoic acid and 2-chlorobenzoic acid, mp. 198-200° C., yield 95% of theory.

Workup

  1. customwas removed in vacuo
  2. temperatureThe mixture was cooled
  3. filtrationthe precipitate filtered off
  4. washwashed with heptane

Sources & evidence

ORD record
ord-c13be4e766324a6fba0aaee9731f52a4
Source dataset
uspto-grants-2012_08
Patent number
US08236986B2

Reaction notes

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