Tetrahydrofuran → Ethyl (2-methoxy-6-nitrophenyl)carbamate

HRID 33387

Reaction equation

HRID 33387 reaction equation
Cl[C:2]([O:5][C:6](Cl)=[O:7])(Cl)Cl.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:12]=1[NH2:20].[CH2:21]1COCC1>>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:12]=1[NH:20][C:6](=[O:7])[O:5][CH2:2][CH3:21]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10426DiphosgeneHCID 854916-Nitro-o-anisidine

Product 1

HCID 86603972Ethyl (2-methoxy-6-nitrophenyl)carbamate

Procedure

17.1 mL (0.141 mol) trichloromethylchloroformate are added dropwise at reflux temperature to a solution of 23.8 g (0.142 mol) 2-methoxy-6-nitro-phenylamine in 300 mL THF and then the mixture is stirred for 4 hours at this temperature. The solvent is distilled off and the residue is stirred with isopropanol, during which time a yellow solid is precipitated. Yield: 25.0 g (73%); mass spectroscopy: [M+H]+=241.

Workup

  1. distillationThe solvent is distilled off
  2. stirringthe residue is stirred with isopropanol, during which time a yellow solid
  3. customis precipitated

Sources & evidence

ORD record
ord-5731544a9aa245a3966584cf36fb4237
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Linked notes

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