3-Chlorobenzenesulphonyl chloride → HCID 68406619, compound

HRID 2241155Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:26])[C:13]2[CH:18]=[C:17]([N+:19]([O-])=O)[C:16]([O:22][CH3:23])=[C:15]([O:24][CH3:25])[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].[Cl:28][C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:26])[C:13]2[CH:14]=[C:15]([O:24][CH3:25])[C:16]([O:22][CH3:23])=[C:17]([NH:19][S:35]([C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([Cl:28])[CH:30]=3)(=[O:37])=[O:36])[CH:18]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

Reactant 2

HCID 179093-Chlorobenzenesulphonyl chloride

HCID 67549363HCID 67549363, compound

Product 1

HCID 68406619HCID 68406619, compound

Procedure

4-[3-(3-Chloro-benzenesulfonylamino)-4,5-dimethoxy-benzoylamino]-benzoic acid, MS (ISP): m/e=489.2 (M+H+), was prepared in analogy to example 1, steps A to D. Step A was performed using 3,4-dimethoxy-5-nitro-benzoyl chloride and yielded 4-(3,4-dimethoxy-5-nitro-benzoylamino)-benzoic acid ethyl ester. This was reduced to 4-(3,4-dimethoxy-5-nitro-benzoylamino)-benzoic acid ethyl ester in step B. This was coupled with 3-chloro-benzenesulfonyl chloride in step C, yielding 4-[3-(3-chloro-benzenesulfonylamino)-4,5-dimethoxy-benzoylamino]-benzoic acid ethyl ester, which was hydrolyzed in step D.

Sources & evidence

ORD record: ord-db602d21e8324e29897c3fad5b08b54b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723538B2

Reaction notes

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