Thiophosgene → 2-(3-Chlorophenyl)-2-(4-nitrophenyl)ethyl Isothiocyanate

HRID 1644553Notes

Reaction equation

HRID 1644553 reaction equation
[C:1](Cl)(Cl)=[S:2].C(=O)(O)[O-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH2:18][NH2:19])[CH:14]=[CH:15][CH:16]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH2:18][N:19]=[C:1]=[S:2])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 667727032-(3-Chlorophenyl)-2-(4-nitrophenyl)ethylamine

Product 1

HCID 866301242-(3-Chlorophenyl)-2-(4-nitrophenyl)ethyl Isothiocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.192 mmol of thiophosgene in 5 ml of methylene chloride was added to an aqueous solution of 2.71 mmol of sodium bicarbonate. Then, over the course of 15 minutes, a mixture of 1.084 mmol of 2-(3-chlorophenyl)-2-(4-nitrophenyl)ethylamine was added dropwise to this mixture. After removal of the organic phase and extraction of the aqueous phase once again with dichloromethane, the combined organic phases were washed with water and the solvent was removed by distillation under reduced pressure in a Rotavapor. The reddish oily 2-(3-chlorophenyl)-2-(4-nitrophenyl)ethyl isothiocyanate was stored in a closed vessel with exclusion of moisture in a refrigerator until processed further.

Workup

  1. additionwas added dropwise to this mixture
  2. customAfter removal of the organic phase and extraction of the aqueous phase once again with dichloromethane
  3. washthe combined organic phases were washed with water
  4. customthe solvent was removed by distillation under reduced pressure in a Rotavapor
  5. customThe reddish oily 2-(3-chlorophenyl)-2-(4-nitrophenyl)ethyl isothiocyanate was stored in a closed vessel with exclusion of moisture in a refrigerator

Sources & evidence

ORD record
ord-00c1e1a7121b4585bedef6939e104ae3
Source dataset
uspto-grants-2012_02
Patent number
US08124621B2

Reaction notes

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