Dimethylformamide → HCID 178477162, compound

HRID 1707423Notes

Reaction equation

HRID 1707423 reaction equation
[Na].[NH:2]1[CH:6]=[C:5]([SH:7])[N:4]=[N:3]1.[S:8]1[CH:12]=C[CH:10]=[C:9]1CC(OCCl)=O.CN(C)C=[O:22]>O>[C:9]([S:8][CH2:12][S:7][C:5]1[N:4]=[N:3][NH:2][CH:6]=1)(=[O:22])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 57186933Chloromethyl thiolacetateHCID 178527739HCID 178527739, compound

Product 1

HCID 178477162HCID 178477162, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 1,2,3-triazole-4-thiol sodium salt (38 g: 309 mMol.) in dimethylformamide (150 ml) at -20° C. is added dropwise chloromethyl thiolacetate (37.4 g: 300 mMol.) over 10 minutes, and the mixture is stirred at the same temperature for 30 minutes and at room temperature for 2 hours, diluted with water and extracted with ethyl acetate. The extract is washed with water, aqueous sodium hydrogen carbonate, and water, dried over sodium sulfate, and concentrated under reduced pressure. The crystalline residue is washed with hexane, dried, and recrystallized from ether to give 4-acetylthiomethylthio-1,2,3-triazole (38.9 g). Yield: 69%. mp. 88° to 89° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water, aqueous sodium hydrogen carbonate, and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe crystalline residue is washed with hexane
  6. customdried
  7. customrecrystallized from ether

Sources & evidence

ORD record
ord-869c83d7a4f342b9a7564197938df829
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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