Benzyl Bromide → 1,3,4-THIADIAZOLE, 2-METHYL-5-[(PHENYLMETHYL)THI

HRID 2413334Notes

Reaction equation

HRID 2413334 reaction equation
[SH:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][N:3]=1.CN(C)P(=O)(N(C)C)N(C)C.C[Si](C)(C)N[Si](C)(C)C.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[CH2:28]([S:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][N:3]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 12679HexamethylphosphoramideHCID 13838HexamethyldisilazaneHCID 178434161HCID 178434161, compound

Product 1

HCID 51582181,3,4-THIADIAZOLE, 2-METHYL-5-[(PHENYLMETHYL)THI

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.0 mg (0.004 mmoles) of di-4-nitrophenyl N-(4-toluenesulfonyl)phosphoramidate were added to a solution of 264 mg (2 mmoles) of 5-mercapto-2-methyl-1,3,4-thiadiazole in 5 ml of toluene and 1.06 ml (6.1 mmoles) of hexamethylphosphoric triamide and then while refluxing, 0.50 ml (2.4 mmoles) of hexamethyldisilazane were added. After refluxing for 1.5 hours, the solution was evaporated to dryness and the residue was dissolved in 4 ml of acetonitrile. 0.28 (2.3 mmoles) of benzyl bromide were added to the solution and it was established that the conversion was complete after stirring for 10 minutes. HPLC analysis of the reaction mixture indicated a quantitative yield of 5-benzylthio-2-methyl-1,3,4-thiadiazole.

Workup

  1. temperaturewhile refluxing
  2. temperatureAfter refluxing for 1.5 hours
  3. customthe solution was evaporated to dryness
  4. dissolutionthe residue was dissolved in 4 ml of acetonitrile

Sources & evidence

ORD record
ord-b9d71ce686aa45daa05b0f01feeb1238
Source dataset
uspto-grants-1985_01
Patent number
US04496720

Reaction notes

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