2-Cyanobenzenesulfonamide → HCID 18971380, compound

HRID 2395308Notes

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([NH:13][C:14]([O:16]C2C=CC=CC=2)=O)[CH:3]=1.[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH2:34])(=[O:33])=[O:32])#[N:24]>>[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH:34][C:14]([NH:13][C:4]1[CH:3]=[C:2]([Cl:1])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:16])(=[O:33])=[O:32])#[N:24]

Participants

Reactant 2

HCID 15110752-Cyanobenzenesulfonamide

HCID 22347443HCID 22347443, compound

Product 1

HCID 18971380HCID 18971380, compound

Procedure

As the starting substances, ethyl 4-chloro-2-phenoxycarbonylaminobenzoate and 2-cyanobenzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-(2-cyanobenzenesulfonyl)-N'-(2-ethyloxycarbonyl-5-chlorophenyl)urea and further to obtain from 1.52 g (3.73 mmol) of N-(2-cyanobenzenesulfonyl)-N'-(2-carboxyl-5-chlorophenyl)urea 810 mg of the above-identified compound (yield 60.1%). Properties: colorless crystal, Melting point: 160°-161° C., PMR (δppm, DMSO-d6):3.71 (3H,s), 6.61 (1H,s), 6.90 (1H,s), 7.12 (1H,s), 7.23 (1H,d), 7.72 (1H,s), 7.86 (1H,d), 11.59 (1H,br).

Sources & evidence

ORD record: ord-d5ecfe940c3045ad84f043323c5cad11
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05814631

Reaction notes

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