Chloroacetyl chloride → 2-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide

HRID 623322Notes

Reaction equation

HRID 623322 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH2:12])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[Cl:19][CH2:20][C:21](Cl)=[O:22]>CN(C=O)C>[Cl:19][CH2:20][C:21]([NH:12][C:10]1[S:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]=1)=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 2194082-Amino-5-phenyl-1,3,4-thiadiazole

Product 1

HCID 51300772-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-phenyl-1,3,4-thiadiazol-2-amine (C1, 1.06 g, 6 mmol) and K2CO3 (0.83 g, 6 mmol) in anhydrous DMF (20 mL), was added chloroacetyl chloride (C2, 0.48 mL, 6 mmol). The mixture was stirred at room temperature for 4 h. The reaction mixture was then poured into ice-water (100 mL), stirred, and then filtered. The resulting solid was washed with water, and then dried in the oven under vacuum to afford compound C3 (1.15 g, 76%) as a white solid.

Workup

  1. stirringstirred
  2. filtrationfiltered
  3. washThe resulting solid was washed with water
  4. customdried in the oven under vacuum

Sources & evidence

ORD record
ord-3557c05a9a394a9a81d330b356a4fbbc
Source dataset
uspto-grants-2016_04
Patent number
US09301949B2

Reaction notes

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