3-Cyclopropylaniline → (3-Cyclopropyl-phenyl)-(6-nitro-4H-benzo[d][1,3]oxazin-2-yl)-amine

HRID 1695669Notes

Reaction equation

C([Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[N:19]=[C:20]=S)(C)C)(C)(C)C.[CH:22]1([C:25]2[CH:26]=[C:27]([NH2:31])[CH:28]=[CH:29][CH:30]=2)[CH2:24][CH2:23]1>>[CH:22]1([C:25]2[CH:26]=[C:27]([NH:31][C:20]3[O:8][CH2:9][C:10]4[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=4[N:19]=3)[CH:28]=[CH:29][CH:30]=2)[CH2:24][CH2:23]1

Participants

Reactant 2

HCID 120321393-Cyclopropylaniline

HCID 46855450tert-Butyl-(2-isothiocyanato-5-nitro-benzyloxy)-dimethyl-silane

Product 1

HCID 67277073(3-Cyclopropyl-phenyl)-(6-nitro-4H-benzo[d][1,3]oxazin-2-yl)-amineYield 74%

Procedure

Prepared from tert-butyl-(2-isothiocyanato-5-nitro-benzyloxy)-dimethyl-silane (Example C1) (5.8 g, 18 mmol) and 3-cyclopropyl-phenylamine (2.5 g, 19 mmol) according to the procedure described for Example 1. Obtained the title compound as a yellow foam (4.1 g, 74%), MS (ISP) m/e=310.5 [(M+H)+].

Sources & evidence

ORD record: ord-f1f456346a0246368e05ce5ef33221b9
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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