1-Chloro-4-(chloromethyl)benzene → 5-(((4-Chlorophenyl)methyl)thio)-1,3,4-thiadiazol-2-amine

HRID 1073777Notes

Reaction equation

HRID 1073777 reaction equation
[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[OH-].[Na+].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1>O.C(O)C>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 178509208HCID 178509208, compound

Product 1

HCID 3518875-(((4-Chlorophenyl)methyl)thio)-1,3,4-thiadiazol-2-amineYield 97.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In 35 ml of water and 70 ml of ethanol, 12.8 g of 2-amino-5-mercapto-1,3,4-thiadiazol and 43 g of sodium hydroxide were added. To this mixture, 14.8 g of 4-chlorobenzyl chloride was added and the mixture was stirred at room temperature for 1 hour. Water was added and the reaction mixture was filtered The residue was washed with water and an ethanol/n-hexane (1:1) mixture, and was dried under reduced pressure, and thus 23.1 g of 2-amino-5-(4-chlorobenzylthio)-1,3,4-thiadiazole was obtained. m.p. 162°~164° C. Yield 93%.

Workup

  1. filtrationthe reaction mixture was filtered The residue
  2. washwas washed with water
  3. dry with materialan ethanol/n-hexane (1:1) mixture, and was dried under reduced pressure

Sources & evidence

ORD record
ord-e7a6689dd6b04249886306f2f9ec08ed
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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