2-Amino-4-chlorobenzoic acid → 7-choro-3-(4-fluorobenzenesulfonyl)-2,4(1H,3H)-quinazolinedione

HRID 2395279Notes

Reaction equation

HRID 2395279 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O>>[Cl:24][C:22]1[CH:23]=[C:15]2[C:16]([C:17](=[O:19])[N:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])[C:12](=[O:13])[NH:14]2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 666462-Amino-4-chlorobenzoic acidHCID 27333744-Fluorobenzenesulfonyl isocyanate

Product 1

HCID 189714877-choro-3-(4-fluorobenzenesulfonyl)-2,4(1H,3H)-quinazolinedioneYield 26.8%

Procedure

1.72 g (8.57 mmol) of 4-fluorobenzenesulfonylisocyanate and 1.47 g (8.57 mmol) of 2-amino-4-chlorobenzoic acid were treated in the same way as in Example 1 to obtain 815 mg of the above-identified compound (yield 26.8%). Properties: colorless crystal, Melting point: >250° C., PMR (δppm, DMSO-d6): 7.12 (1H,s), 7.23 (1H,d), 7.49-7.55 (2H,m), 7.86 (1H,d), 8.23-8.28 (2H,m), 11.90 (1H,br).

Sources & evidence

ORD record
ord-490dd0aeab1c4a55a9e11b1c31315ca7
Source dataset
uspto-grants-1998_09
Patent number
US05814631

Reaction notes

Loading…