2-Amino-4-chlorobenzoic acid → 7-chloro-3-(2,5-dichlorobenzenesulfonyl)-2,4(1H,3H)-quinazolinedione

HRID 2395299Notes

Reaction equation

HRID 2395299 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][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[CH:4]=[C:5]([Cl:8])[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 128751872,5-Dichlorobenzene-1-sulfonyl isocyanate

Product 1

HCID 189715007-chloro-3-(2,5-dichlorobenzenesulfonyl)-2,4(1H,3H)-quinazolinedioneYield 59.1%

Procedure

1.12 g (4.42 mmol) of 2,5-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 1.06 g of the above-identified compound (yield 58.6%). Properties: colorless crystal, Melting point: 254°-256° C., PMR (δppm, DMSO-d6):7.17 (1H,s), 7.24 (1H,d), 7.71 (1H,d), 7.80-7.89 (2H,m), 8.18 (1H,s).

Sources & evidence

ORD record
ord-93de32124e154be594180ce65a70a71d
Source dataset
uspto-grants-1998_09
Patent number
US05814631

Reaction notes

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