Nitromethane → tert-Butyl [1-(2-chlorophenyl)-2-nitroethyl]carbamate
Reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].C(N(CC)C(C)C)(C)C.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1/[CH:21]=[N:22]/[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:4][N+:1]([O-:3])=[O:2]Participants
4
Procedure
A quantity of 16 ml (295.41 mmol) of nitromethane was admixed with 436 μl (2.50 mmol) of N,N-diisopropylethylamine and the yellow solution was stirred at RT for 1 h. Then 2.0 g (8.34 mmol) of the compound from Example 111A were added and the mixture was stirred overnight at RT. All of the volatile constituents were removed on a rotary evaporator. The residue was dissolved in 9 ml of isopropanol in the heat of boiling, and the solution was then cooled to 0° C. The white solid precipitated was filtered off with suction and washed with a little cold isopropanol. Drying in an HV gave 1.18 g (47% of theory) of the title compound.
Workup
- stirringthe mixture was stirred overnight at RT
- customAll of the volatile constituents were removed on a rotary evaporator
- dissolutionThe residue was dissolved in 9 ml of isopropanol in the
- temperatureheat
- temperaturethe solution was then cooled to 0° C
- customThe white solid precipitated
- filtrationwas filtered off with suction
- washwashed with a little cold isopropanol
- customDrying in an HV
Sources & evidence
- ORD record
- ord-a5a26bff30d543a683fbc4ce08101a85
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796324B2
Reaction notes
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