Ethyl chloroformate → HCID 20349074, compound

HRID 1449309Notes

Reaction equation

HRID 1449309 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][OH:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)(O)[O-].[Na+].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].O1CCO[CH2:25][CH2:24]1>O>[CH2:24]([CH:21]([CH3:22])[O:20][C:18](=[O:19])[N:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[OH:11])[CH3:25]

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 5487858Benzenamine, N-hydroxy-3-nitro-

Product 1

HCID 20349074HCID 20349074, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of N-(m-nitrophenyl) hydroxylamine (19.0 g.) in dioxane (100 ml.), water (25 ml.) and sodium bicarbonate (11.0 g.) was cooled to 5° C. Ethyl chloroformate (13.3 g; 11.8 ml.) was added to the solution and the mixture stirred at 5° C. for about 1/2 hour. The reaction mixture was poured into ice water (300 ml.) and the precipitate therefrom was removed by filtering and was dried by standing. The solid product was recrystallized from benzene-hexane mixture and dried under vacuum to yield ethyl (3-nitrophenyl)-N-hydroxyurethane as yellow crystals melting 103°-105° C.

Workup

  1. customthe precipitate therefrom was removed
  2. filtrationby filtering
  3. customwas dried
  4. customThe solid product was recrystallized from benzene-hexane mixture
  5. customdried under vacuum

Sources & evidence

ORD record
ord-79478838332541aaa580d44d1dbf2b1f
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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