Water → HCID 19919994, compound

HRID 1648415Notes

Reaction equation

HRID 1648415 reaction equation
[Cl:1][C:2]1[C:3]([S:12][CH2:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[NH2:16])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.N1C=CC=CC=1.Cl[C:28]([O:30][CH3:31])=[O:29].O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([S:12][CH2:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[NH:16][C:28](=[O:29])[O:30][CH3:31])=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 19920000HCID 19920000, compound

Product 1

HCID 19919994HCID 19919994, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2.23 g of 2-(3-chloro-5-trifluoromethyl-2-pyridylthiomethyl)aniline and 0.83 g of pyridine in 10 ml of toluene was drop-wise added to a solution of 1.1 g of methyl chloroformate in 10 ml of toluene under stirring at 10° to 15° C. After completion of the drop-wise addition, the reaction was continued at room temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into water, subjected to extraction with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was washed with hexane. The precipitated solid was filtered off to obtain 1.9 g of the desired product (Compound No. 1) having a melting point of 111° to 113° C.

Workup

  1. additionAfter completion of the drop-wise addition
  2. customAfter completion of the reaction
  3. extractionsubjected to extraction with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washThe resulting residue was washed with hexane
  8. filtrationThe precipitated solid was filtered off

Sources & evidence

ORD record
ord-d244b057a7984229892048840cf7d91f
Source dataset
uspto-grants-1995_07
Patent number
US05436267

Reaction notes

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