Calcium Carbonate → 3-Chloropropyl (4-hydroxy-2-nitrophenyl)carbamate

HRID 482674

Reaction equation

HRID 482674 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[NH2:10])([O-:3])=[O:2].C(=O)([O-])[O-].[Ca+2].Cl[C:18]([O:20][CH2:21][CH2:22][CH2:23][Cl:24])=[O:19]>C(COC)OC>[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[NH:10][C:18](=[O:19])[O:20][CH2:21][CH2:22][CH2:23][Cl:24])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 202445903-Chloropropyl (4-hydroxy-2-nitrophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

77 g (0.5 mole) of 3-nitro-4-aminophenol are dissolved in 200 ml of dimethoxy ethane, 27 g of calcium carbonate are added, and 80 g (0.51 mole) of γ-chloropropyl chloroformate are added dropwise at 70° C. After 1 hour, the reaction mixture is filtered hot and the filtrate is stirred into 700 ml of ice-water, after which 128 g (93%) of the desired compound precipitate. The melting point is 103°-105° C., and after recrystallisation from toluene is 106° C.

Workup

  1. filtrationthe reaction mixture is filtered hot
  2. customThe melting point is 103°-105° C., and after recrystallisation from toluene
  3. customis 106° C.

Sources & evidence

ORD record
ord-f7719ddf30034dadbe3f7e7ec4fec665
Source dataset
uspto-grants-1986_03
Patent number
US04575378

Linked notes

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