Sulfanilamide → Methyl 2-{[(4-aminobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoate

HRID 2395313Notes

Reaction equation

HRID 2395313 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][C:13]([O:15]C2C=CC=CC=2)=O)[CH:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>>[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:13]([NH:12][C:4]2[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[O:15])(=[O:30])=[O:31])=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 5333SulfanilamideHCID 15524163HCID 15524163, compound

Product 1

HCID 22347486Methyl 2-{[(4-aminobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoate

Procedure

As the starting substances, methyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-aminobenzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-(4-aminobenzenesulfonyl)-N'-(2-methoxycarbonyl-5-chlorophenyl)urea and further to obtain from 470 mg (1.27 mmol) of N-(4-aminobenzenesulfonyl)-N'-(2-carboxy-5-chlorophenyl)urea 270 mg of the above-identified compound (yield 60.5%). Properties: colorless crystal, Melting point: >250° C. (decomposition), PMR (δppm, DMSO-d6):6.39 (2H,s), 6.63 (2H,d), 7.09 (1H,s), 7.22 (2H,d), 7.76 (2H,d), 7.83 (2H,d), 11.51 (1H,s).

Sources & evidence

ORD record
ord-1780a2bfb84042eb8d670796e8b1f1d1
Source dataset
uspto-grants-1998_09
Patent number
US05814631

Reaction notes

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