2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine → (2,2-Dimethyl-2,3-dihydro-benzofuran-7-yl)-(6-nitro-4H-benzo[d][1,3]oxazin-2-yl)-amine

HRID 1695687Notes

Reaction equation

HRID 1695687 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.[NH2:22][C:23]1[C:31]2[O:30][C:29]([CH3:33])([CH3:32])[CH2:28][C:27]=2[CH:26]=[CH:25][CH:24]=1>>[CH3:32][C:29]1([CH3:33])[CH2:28][C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([NH:22][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)[C:31]=2[O:30]1

Participants

3

Reactant 2

HCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amineHCID 46855450tert-Butyl-(2-isothiocyanato-5-nitro-benzyloxy)-dimethyl-silane

Product 1

HCID 67277608(2,2-Dimethyl-2,3-dihydro-benzofuran-7-yl)-(6-nitro-4H-benzo[d][1,3]oxazin-2-yl)-amineYield 67%

Procedure

Prepared from tert-butyl-(2-isothiocyanato-5-nitro-benzyloxy)-dimethyl-silane (Example C1) (3.75 g, 11 mmol) and 7-amino-2,3-dihydro-2,2-dimethylbenzofuran (CAS 68298-46-4) (1.86 g, 11 mmol) according to the procedure described for Example 1. Obtained the title compound as a yellow solid (2.5 g, 65%), MS (ISP) m/e=340.3 [(M+H)+].

Sources & evidence

ORD record
ord-602450a963ca496394bf4915a5eeb1af
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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