Water → beta-chloroethyl N-(5-chloro-4-hydroxy-2-nitrophenyl)-carbamate

HRID 482677Notes

Reaction equation

HRID 482677 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][Cl:7])=[O:3].[Cl:8][C:9]1[C:14]([OH:15])=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[C:11]([NH2:19])[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1>[Cl:8][C:9]1[C:14]([OH:15])=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[C:11]([NH:19][C:2](=[O:3])[O:4][CH2:5][CH2:6][Cl:7])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 123052-Chloroethyl chloroformateHCID 189506174-Amino-2-chloro-5-nitrophenol

Product 1

HCID 20244604beta-chloroethyl N-(5-chloro-4-hydroxy-2-nitrophenyl)-carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

21 ml of β-chloroethyl chloroformate are added dropwise to 37.7 g (0.2 mole) of 6-chloro-3-nitro-4-aminophenol and 12 g of sodium carbonate in 130 ml of dioxane at 70° C. and the mixture is then heated at 90° C. for a further hour. After addition of 500 ml of water and stirring until cold, the mixture is extracted 3 times with methylene chloride and the extracts are dried and concentrated completely, after which 56 g (95%) of the product are obtained as a dark red oil, which crystallises completely, after some time, by trituration with toluene.

Workup

  1. extractionis extracted 3 times with methylene chloride
  2. customthe extracts are dried
  3. concentrationconcentrated completely

Sources & evidence

ORD record
ord-4b805e83c53f40afad26994c52f48ea0
Source dataset
uspto-grants-1986_03
Patent number
US04575378

Reaction notes

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