Potassium Carbonate → HCID 14881545, compound

HRID 704375Notes

Reaction equation

HRID 704375 reaction equation
[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2596681-Bromo-4-phenylbutaneHCID 178509208HCID 178509208, compound

Product 1

HCID 14881545HCID 14881545, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 320 mg of 2-amino-5-mercapto-1,3,4-thiadiazole, 430 mg of 1-bromo-4-phenylbutane and 350 mg of potassium carbonate in 5 ml of N,N-dimethylformamide was stirred overnight at room temperature. After dilution with ethyl acetate, the reaction mixture was washed in sequence with water, 1N sodium hydroxide, water and saturated aqueous solution of sodium chloride, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was recrystallized from ethyl acetate to give 300 mg of 2-amino-5-[(4-phenylbutyl)thio]-1,3,4-thiadiazole. Melting point 111° C.

Workup

  1. washAfter dilution with ethyl acetate, the reaction mixture was washed in sequence with water, 1N sodium hydroxide, water and saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-079c3451b3b34f52996b502b39c551db
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

Loading…