2-Aminobenzenesulfonamide → 3-(2-Aminobenzenesulfonyl)-7-Chloro-2,4(1H,3H)-Quinazolinedione

HRID 2301292Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[Cl:12][C:13]1[CH:14]=[C:15]([NH:23][C:24](OC2C=CC=CC=2)=[O:25])[C:16](=[CH:21][CH:22]=1)[C:17](OC)=[O:18]>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:17](=[O:18])[C:16]2[C:15](=[CH:14][C:13]([Cl:12])=[CH:22][CH:21]=2)[NH:23][C:24]1=[O:25])(=[O:9])=[O:10]

Participants

Reactant 2

HCID 728942-Aminobenzenesulfonamide

HCID 15524163HCID 15524163, compound

Product 1

HCID 98413923-(2-Aminobenzenesulfonyl)-7-Chloro-2,4(1H,3H)-QuinazolinedioneYield 58%

Procedure

2.7 g (15.7 mmol) of 2-aminobenzenesulfonamide and 4.8 g (15.7 mmol) of methyl 4-chloro-2-N-phenoxycarbonylanthranilate were treated in the same way as Preparation Example 1 to obtain 3.2 g (yield 58%: 3 steps) of the above-identified compound. Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δ ppm, DMSO-d6): 6.46 (2H, s), 6.65 (1H, t), 6.81 (1H, d), 7.12 (1H, s), 7.23 (1H, d), 7.34 (1H, t), 7.76 (1H, d), 7.86 (1H, d).

Workup

customto obtain 3.2 g (yield 58%: 3 steps) of the above-identified compound

Sources & evidence

ORD record: ord-f68b8749d0444b1083aab5947ff2b172
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500835B2

Reaction notes

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