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

HRID 477733Notes

Reaction equation

HRID 477733 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[NH:10][N:9]=[C:8]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]=1.C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl>[C:1]([N:10]1[C:6]([NH2:5])=[N:7][C:8]([S:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:9]1)(=[O:3])[CH3:2]

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-triazoleYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (12.57 g) in methylene chloride (30 ml) was added to the product of stage (a) (30 g) and triethylamine (25 ml) in methylene chloride (300 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. It was then treated with 1N sodium hydroxide (160 ml) and extracted with methylene chloride. The product, after drying, was recrystallised from ethyl acetate to give 33 g of the desired product, mp 146° C.

Workup

  1. extractionextracted with methylene chloride
  2. customThe product, after drying
  3. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-8b4bbebfa07e425ea0077ae1d86b72c5
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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