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

HRID 477740Notes

Reaction equation

HRID 477740 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.[OH-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[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 3

HCID 6367Acetyl chlorideHCID 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 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Acetyl chloride (12.57 g) in methylene chloride (30 ml) was added to the product of stage (a) (30 g) in triethylamine (25 ml) and methylene chloride (300 ml) at 0° C., and the mixture was stirred for 30 minutes. Then 1N sodium hydroxide was added, and the solution was extracted with methylene chloride. On drying, and recrystallisation from ethyl acetate, 33 g of the desired product, mp 146° C., were obtained.

Workup

  1. extractionthe solution was extracted with methylene chloride
  2. customOn drying
  3. customrecrystallisation from ethyl acetate, 33 g of the desired product, mp 146° C.
  4. customwere obtained

Sources & evidence

ORD record
ord-57814ae2c7a04ef7a48bcf4cf2092c22
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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