Benzyl Bromide → HCID 178420431, compound

HRID 537267Notes

Reaction equation

HRID 537267 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[C:13]([S-:14])=[CH:12][N:11]=[N:10]1.[Na+]>C(O)C.C(OCC)(=O)C>[CH2:1]([S:14][C:13]1[N:9]=[N:10][NH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178507106HCID 178507106, compound

Product 1

HCID 178420431HCID 178420431, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromide (11.79 ml, 99 mmol) was added dropwise to a solution of sodium 1H-1,2,3-triazole-5-thiolate (12.2 g, 99 mmol) in ethanol (100 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 20 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (100 mL), brine (100 mL) and dried (sodium sulphate). The solvent was removed to give 4-(benzylthio)-1H-1,2,3-triazole (16.9 g) as a white solid. LCMS (Method F, ES-API): RT 1.66 min, m+H=191.9; 1H NMR (400 MHz, CDCl3): δ 9.72 (1H, v br s), 7.47 (1H, s), 7.30-7.21 (5H, m), 4.12 (2H, s).

Workup

  1. washwashed with water (100 mL), brine (100 mL)
  2. dry with materialdried (sodium sulphate)
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-a772ae1ff1694cd38dbd13a762629fb3
Source dataset
uspto-grants-2014_10
Patent number
US08859774B2

Reaction notes

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