7-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one → Methyl 4-nitro-5-((3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)oxy)thiophene-2-carboxylate

HRID 1192259Notes

Reaction equation

HRID 1192259 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[CH2:8][O:7][C:6]=2[CH:12]=1.Cl[C:14]1[S:18][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]>>[N+:23]([C:15]1[CH:16]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[S:18][C:14]=1[O:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[CH2:8][O:7][C:6]=2[CH:12]=1)([O-:25])=[O:24]

Participants

3

Reactant 2

HCID 100578707-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 13205564Methyl 5-chloro-4-nitrothiophene-2-carboxylate

Product 1

HCID 67494597Methyl 4-nitro-5-((3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)oxy)thiophene-2-carboxylate

Procedure

Prepared according to the procedure described for step A of example 18 from 7-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one (826 mg, 5.0 mmol) and methyl 5-chloro-4-nitro-thiophene-2-carboxylate (1.1 g, 5.0 mmol). The title compound was obtained as a white solid (400 mg, 23% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.92 (1H, S), 8.04 (1H, S), 7.22 (1H, M), 7.10 (2H, S), 7.03 (1H, M), 4.66 (2H, S), 3.80 (3H, S). MS m/z: 349.20 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ea9ba7e958344465b3b90cbbad36fd5e
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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