Benzyl Bromide → HCID 178420431, compound

HRID 920639Notes

Reaction equation

HRID 920639 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-87fb0b7fdcb54b7d911ee8c497031cd4
Source dataset
uspto-grants-2016_03
Patent number
US09273047B2

Reaction notes

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