Water → Ethyl 4-chloro-3-cyanophenylcarbamate

HRID 2355759Notes

Reaction equation

HRID 2355759 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:16])=[C:12]([CH:15]=1)[C:13]#[N:14].N1C=CC=CC=1.O>C(Cl)Cl>[Cl:16][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:2](=[O:3])[O:4][CH2:5][CH3:6])=[CH:15][C:12]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 109972345-Amino-2-chlorobenzonitrile

Product 1

HCID 60705219Ethyl 4-chloro-3-cyanophenylcarbamateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl chloroformate (3.68 g) in methylene chloride (5 ml) is added dropwise in about 20 minutes to a mixture of 5-amino-2-chlorobenzonitrile (5.2 g) and pyridine (2.77 g) in methylene chloride (75 ml), cooled to 0° C. and maintained in an inert atmosphere. At the end of the addition, the solution is stirred for 1 hour at 0° C. and is then brought to room temperature. At the end of the reaction, the mixture is poured into water (100 ml) and extracted with methylene chloride (2×80 ml); the organic phase is washed with water (2×80 ml), dried with sodium sulphate and concentrated under vacuum. 7.2 g of product are obtained.

Workup

  1. temperaturemaintained in an inert atmosphere
  2. additionAt the end of the addition
  3. customis then brought to room temperature
  4. customAt the end of the reaction
  5. extractionextracted with methylene chloride (2×80 ml)
  6. washthe organic phase is washed with water (2×80 ml)
  7. dry with materialdried with sodium sulphate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d304c6e19ad741f489805e226c057952
Source dataset
uspto-grants-2010_07
Patent number
US07754880B2

Reaction notes

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