Benzyl Bromide → 1,3,4-Thiadiazol-2-amine, 5-((phenylmethyl)thio)-

HRID 1416221Notes

Reaction equation

HRID 1416221 reaction equation
[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[K+]>CO>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 178509208HCID 178509208, compound

Product 1

HCID 992851,3,4-Thiadiazol-2-amine, 5-((phenylmethyl)thio)-Yield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-5-mercapto-1,3,4-thiadiazole (2.0 g), benzyl bromide (2.6 g), and potassium hydroxide (0.8 g) were stirred in methanol (50 ml) overnight at room temperature. The reaction mixture was concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The resulting solid was recrystallized from n-hexane/ethanol, thereby yielding 2.4 g of the aimed compound.

Workup

  1. concentrationThe reaction mixture was concentrated under a vacuum
  2. additionThe residue, with water added
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe resulting solid was recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-6b6b2345173e4f18bfe414b1ac6105be
Source dataset
uspto-grants-1999_06
Patent number
US05912258

Reaction notes

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