Calcium Carbonate → gamma-chloropropyl N-(5-chloro-4-hydroxy-2-nitrophenyl)-carbamate

HRID 482678

Reaction equation

HRID 482678 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:12])[CH:3]=1.C(=O)([O-])[O-].[Ca+2].Cl[C:19]([O:21][CH2:22][CH2:23][CH2:24][Cl:25])=[O:20]>C(COC)OC>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH:12][C:19](=[O:20])[O:21][CH2:22][CH2:23][CH2:24][Cl:25])[CH:3]=1

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 189506174-Amino-2-chloro-5-nitrophenol

Product 1

HCID 20244610gamma-chloropropyl N-(5-chloro-4-hydroxy-2-nitrophenyl)-carbamate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

37.7 g (0.2 mole) of 6-chloro-3-nitro-4-aminophenol are dissolved in 120 ml of dimethoxyethane, 11 g of calcium carbonate are added and 32 g of γ-chloropropyl chloroformate are added dropwise at 70° C. After 1 hour at 90° C., the mixture is filtered hot and the filtrate is stirred into 300 ml of ice-water. The initially oily product crystallises after a short time.

Workup

  1. filtrationthe mixture is filtered hot
  2. customThe initially oily product crystallises after a short time

Sources & evidence

ORD record
ord-d7662345536f47cfb421a57164b00f62
Source dataset
uspto-grants-1986_03
Patent number
US04575378

Linked notes

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