Acetyl chloride → 1-Acetyl-5-amino-3-benzylthio-1,2,4-triazole

HRID 1722930Notes

Reaction equation

HRID 1722930 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23].[OH-].[Na+]>C(Cl)Cl>[C:22]([N:6]1[C:2]([NH2:1])=[N:3][C:4]([S:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:5]1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 7372725-(benzylsulfanyl)-4H-1,2,4-triazol-3-amine

Product 1

HCID 142551221-Acetyl-5-amino-3-benzylthio-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 30 g (0.145 mol) 5-amino-3-benzylthio-1H-1,2,4-triazole and 25 ml triethylamine in 300 ml methylene chloride, 12.57 g (0.16 mol) acetyl chloride in 30 ml methylene chloride was added dropwise. It was then stirred at room temperature for 30 minutes, treated with 160 ml 1N caustic soda and the product extracted with methylene chloride. After drying it was recrystallised from ethyl acetate.

Workup

  1. extractionthe product extracted with methylene chloride
  2. customAfter drying it
  3. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-750e84dd79d44b36b62808683548c0fc
Source dataset
uspto-grants-1989_08
Patent number
US04859231

Reaction notes

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