2-Amino-4-chlorobenzoic acid → HCID 22347468, compound

HRID 897016Notes

Reaction equation

HRID 897016 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[Cl:17][C:18]1[CH:19]=[C:20]([NH2:27])[C:21](=[CH:25][CH:26]=1)[C:22](O)=[O:23]>>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C:22](=[O:23])[C:21]3[C:20](=[CH:19][C:18]([Cl:17])=[CH:26][CH:25]=3)[NH:27][C:15]2=[O:16])(=[O:13])=[O:12])=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 666462-Amino-4-chlorobenzoic acidHCID 22347445HCID 22347445, compound

Product 1

HCID 22347468HCID 22347468, compoundYield 54.3%

Procedure

From 1.50 g (7.03 mmol) of 4-allyloxybenzenesulfonyl isocyanate and 1.2 g (7.03 mmol) of 4-chloroanthranilic acid in a similar manner to Preparation Example 5, 1.5 g (yield 53%) of 3-(4-allyloxybenzenesulfonyl)-7-chloro-2,4(1H,3H)-quinazolinedione was obtained. From 500 mg (1.27 mmol) among this, 405 mg of the title compound (yield 90%) was obtained in a similar manner. Property: colorless crystals, melting point: >200° C. (decomposition), PMR (δppm, DMSO-d6): 6.98 (2H, d), 7.11 (1H, s), 7.23 (1H, d), 7.85 (1H, d), 8.00 (2H, d), 11.25 (1H, br).

Sources & evidence

ORD record
ord-fbbf7020428a472e86624204d9d2bdf5
Source dataset
uspto-grants-2005_07
Patent number
US06921766B1

Reaction notes

Loading…