Water → HCID 178452973, compound
Reaction equation
N[N:2]([CH:10]=[NH:11])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])=O.O.C[N:27](C)C=O>>[N+:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[N:27]=[C:10]([NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[NH:11][CH:13]=1)([O-:24])=[O:23]Participants
Procedure
tert-Butyl amino(imino)methylcarbamate (4.78 g; 30 mmol) was dissolved in N,N-dimethylformamide (30 mL), 2-bromo-2′-nitroacetophenone (2.44 g; 10 mmol) was added thereto, and the mixture was stirred for 144 hours at room temperature. To the reaction solution, water (100 mL) was added, and the precipitated powder was collected by filtration. The resulting powder was dissolved in ethyl acetate (200 mL), and the mixture was washed with saturated aqueous sodium bicarbonate solution (two times). The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure. The resulting residue was dispersed in acetone/diethyl ether, collected by filtration and dried to give 1.09 g of the title compound (yield 36%).
Workup
- filtrationthe precipitated powder was collected by filtration
- dissolutionThe resulting powder was dissolved in ethyl acetate (200 mL)
- washthe mixture was washed with saturated aqueous sodium bicarbonate solution (two times)
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- distillationdistilled under reduced pressure
- additionThe resulting residue was dispersed in acetone/diethyl ether
- filtrationcollected by filtration
- customdried
Sources & evidence
- ORD record
- ord-c3eebfe086a849e58b6c7c1c0b55b0db
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975411B2
Reaction notes
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