Benzenesulfonyl chloride → N-[2-(3-Cyclopropyl-phenylamino)-4H-benzo[d][1,3]oxazin-6-yl]-benzenesulfonamide

HRID 1695694Notes

Reaction equation

[CH:1]1([C:4]2[CH:5]=[C:6]([NH:10][C:11]3[O:12][CH2:13][C:14]4[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:15]=4[N:16]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH:1]1([C:4]2[CH:5]=[C:6]([NH:10][C:11]3[O:12][CH2:13][C:14]4[CH:20]=[C:19]([NH:21][S:28]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)(=[O:30])=[O:29])[CH:18]=[CH:17][C:15]=4[N:16]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 59231769N2-(3-cyclopropyl-phenyl)-4H-benzo[d][1,3]oxazine-2,6-diamine

Product 1

HCID 59231883N-[2-(3-Cyclopropyl-phenylamino)-4H-benzo[d][1,3]oxazin-6-yl]-benzenesulfonamideYield 58%

Procedure

Prepared from N2-(3-Cyclopropyl-phenyl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 119) (200 mg, 0.72 mmol) and benzenesulfonyl chloride (139 mg, 0.78 mmol) according to the procedure described for Example 27. Obtained the title compound as an off-white foam (174 mg, 58%), MS (ISP) m/e=420.3 [(M+H)+].

Sources & evidence

ORD record: ord-52d418f373d3486e9def07e1edfc8ec9
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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