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

HRID 703826

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[OH-].[Na+].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O.C(O)C>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5][N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In a mixture of 40 ml of water and 45 ml of ethanol, 21.1 g of 2-amino-5-mercapto-1,3,4-thiadiazole and 6.9 g of sodium hydroxide were dissolved. To this solution, 19.6 g of benzyl chloride was added, and the mixture was stirred at 50° C. for 1 hour. After cooling, water was added to the reaction mixture, the formed precipitate was separated by filtration and washed with water and an ethanol/n-hexane (1:1) mixture respectively. The thus treated precipitate was dried under reduced pressure, and thus 32.5 g of 2-amino-5-benzylthio-1,3,4-thiadiazole was obtained. m.p. 159°-161° C. Yield 94%.

Workup

dissolutionwere dissolved
temperatureAfter cooling
customthe formed precipitate was separated by filtration
washwashed with water
customThe thus treated precipitate was dried under reduced pressure

Sources & evidence

ORD record: ord-384ab92d6add4c6d88eb0e2c8156c0e7
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04985432

Linked notes

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