Triethylamine → 3-(4-Bromo-3-methylphenyl)-5-methyl-1,2,4-triazole

HRID 1741063Notes

Reaction equation

HRID 1741063 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=O)=[CH:4][C:3]=1[CH3:12].Cl.[C:14](=[NH:19])(OCC)[CH3:15].C(N(CC)CC)C>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:19]=[C:14]([CH3:15])[NH:9][N:8]=2)=[CH:4][C:3]=1[CH3:12]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 39058874-Bromo-3-methylbenzohydrazide

Product 1

HCID 218338103-(4-Bromo-3-methylphenyl)-5-methyl-1,2,4-triazoleYield 59.5%

Procedure

4-Bromo-3-methylbenzoic hydrazide (D30, 3.06 g, 13 mmol), ethyl acetimidate hydrochloride (2.48 g, 20 mmol) and triethylamine (5.6 ml, 40 mmol) were stirred at reflux under Ar for 24 h, and then evaporated to dryness. The residue was chromatographed on silica gel, eluting with dichloromethane/ethanol/ammonia (300:8:1). This gave the title compound (1.95 g, 58%) as a white solid.

Workup

  1. temperatureat reflux under Ar for 24 h
  2. customevaporated to dryness
  3. customThe residue was chromatographed on silica gel
  4. washeluting with dichloromethane/ethanol/ammonia (300:8:1)

Sources & evidence

ORD record
ord-b21d4f72032e4fefbcae8baefd5bd2b4
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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