Thiophosgene → HCID 21937476, compound

HRID 1744208Notes

Reaction equation

HRID 1744208 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH-:6].C(=O)(O)[O-].[Na+].[C:18](Cl)(Cl)=[S:19]>ClCCl.O>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][N:6]=[C:18]=[S:19]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 86759946HCID 86759946, compound

Product 1

HCID 21937476HCID 21937476, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution containing 2-trifluoromethylbenzylamide (3.50 g, 0.02 mol) in 50 ml of dichloromethane and a solution containing sodium bicarbonate (3.4 g, 0.04 mol) in 55 ml of water are added simultaneously over one hour at a temperature close to 20° C. to a solution of thiophosgene (2.28 g, 0.02 mol) in 15 ml of dichloromethane. Agitation is carried out for 30 minutes. The reaction mixture is decanted and the organic phase washed with 100 ml of water then with 100 ml of a solution of salt water. The organic phase is dried over magnesium sulphate and the solvent is evaporated off with a rotary evaporator. The expected compound is obtained in the form of an oil (3.50 g, 81%). Considering its reactivity, it is used immediately for the following reaction.

Workup

  1. additionare added simultaneously over one hour at a temperature
  2. customThe reaction mixture is decanted
  3. washthe organic phase washed with 100 ml of water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customthe solvent is evaporated off with a rotary evaporator

Sources & evidence

ORD record
ord-c8fe9dec07094a9fa2ebe587c9855995
Source dataset
uspto-grants-2006_03
Patent number
US07015213B1

Reaction notes

Loading…