Ethyl chloroformate → Ethyl [4-(4-nitrophenoxy)-3-nitrophenyl]carbamate

HRID 1277843Notes

Reaction equation

HRID 1277843 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:22](=[O:23])[O:24][CH2:25][CH3:26])=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 23451853HCID 23451853, compound

Product 1

HCID 53855470Ethyl [4-(4-nitrophenoxy)-3-nitrophenyl]carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

4-(4-Nitrophenoxy)-3-nitrobenzenamine (0.1 mole) and pyridine (50 ml) are charged into a glass reaction vessel fitted with a mechanical stirrer and thermometer and are cooled to about 5° C. Ethyl chloroformate (0.125 mole) is added, with stirring, at about 5° C. Stirring is continued for a period of about 30 minutes at about 5° C., then for an additional 16 hours at room temperature. The mixture is then washed with 2 portions of water (50 ml), dried and the solvent is then removed to yield the desired product ethyl [4-(4-nitrophenoxy)-3-nitrophenyl]carbamate.

Workup

  1. customfitted with a mechanical stirrer
  2. stirringStirring
  3. waitfor an additional 16 hours at room temperature
  4. washThe mixture is then washed with 2 portions of water (50 ml)
  5. customdried
  6. customthe solvent is then removed

Sources & evidence

ORD record
ord-b72fb510706940b2adf21962512940f7
Source dataset
uspto-grants-1981_07
Patent number
US04279637

Reaction notes

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