Benzenesulfonamide, 4-amino-3,5-dichloro- → Methyl 2-{[(4-amino-3,5-dichlorobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoate

HRID 1376265Notes

Reaction equation

HRID 1376265 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[Cl:13].[Cl:14][C:15]1[CH:16]=[C:17]([NH:25][C:26](OC2C=CC=CC=2)=[O:27])[C:18](=[CH:23][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>>[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([S:9]([NH:12][C:26]([NH:25][C:17]2[CH:16]=[C:15]([Cl:14])[CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])=[O:27])(=[O:11])=[O:10])=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 89607Benzenesulfonamide, 4-amino-3,5-dichloro-HCID 15524163HCID 15524163, compound

Product 1

HCID 22347451Methyl 2-{[(4-amino-3,5-dichlorobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoateYield 45.4%

Procedure

1.06 g (4.40 mmol) of 4-amino-3,5-dichlorobenzenesulfonamide and 1.34 g (4.40 mmol) of methyl 4-chloro-2-N-phenoxycarbonylanthranilate were treated in the same way as Example 1 to obtain 905 mg (yield 44%) of methyl 2-{[(4-amino-3,5-dichlorobenzenesulfonylamino)carbonyl]amino}-4-chlorobenzoate. Properties: colorless amorphous, PMR (5 ppm, DMSO-d6): 3.87 (3H, s), 6.59 (2H, br), 7.–22 (1H, dd), 7.72 (2H, s), 7.93 (1H, d), 8.24 (1H, d), 10.17 (1H, s).

Sources & evidence

ORD record
ord-d2345c6346a046a3a7af006c531721cb
Source dataset
uspto-grants-2007_01
Patent number
US07169951B2

Reaction notes

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