2-Amino-4-chlorobenzoic acid → 7-chloro-3-(2,6-dichlorobenzenesulfonyl)-2,4(1H,3H)-quinazolinedione

HRID 2395300Notes

Reaction equation

HRID 2395300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([N:12]=[C:13]=[O:14])(=[O:11])=[O:10].[NH2:15][C:16]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=O>>[Cl:25][C:23]1[CH:24]=[C:16]2[C:17]([C:18](=[O:20])[N:12]([S:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:11])=[O:10])[C:13](=[O:14])[NH:15]2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 666462-Amino-4-chlorobenzoic acidHCID 128751892,6-Dichlorobenzenesulfonyl isocyanate

Product 1

HCID 189714137-chloro-3-(2,6-dichlorobenzenesulfonyl)-2,4(1H,3H)-quinazolinedioneYield 40.5%

Procedure

1.12 g (4.42 mmol) of 2,6-dichlorobenzenesulfonylisocyanate and 882 mg (4.42 mmol) of 2-amino-4-chlorobenzoic acid were treated in the same way as in Example 1 to obtain 725 mg of the above-identified compound (yield 40.5%). Properties: colorless crystal, Melting point: 260°-261° C., PMR (δppm, DMSO-d6):7.18 (1H,s), 7.22 (1H,br), 7.63 (3H,br), 7.88 (1H,d), 11.83 (1H,br).

Sources & evidence

ORD record
ord-f11a6daea7b84a27b8ae87b2dd8a5dc1
Source dataset
uspto-grants-1998_09
Patent number
US05814631

Reaction notes

Loading…