Trityl chloride → 3-Methyl-1-(triphenylmethyl)-1H-1,2,4-triazole

HRID 582160Notes

Reaction equation

HRID 582160 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[N:26]=[CH:25][NH:24][N:23]=1.C(N(CC)CC)C>ClCCl>[C:1]([N:24]1[CH:25]=[N:26][C:22]([CH3:21])=[N:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178433329HCID 178433329, compound

Product 1

HCID 543633743-Methyl-1-(triphenylmethyl)-1H-1,2,4-triazoleYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trityl chloride (19.0 g) was added portionwise to a stirred solution of 3-methyl-1,2,4-triazole (5.6 g, commercial) and triethylamine (9.5 ml) in dichloromethane (200 ml). The mixture was diluted with dichloromethane (100 ml), washed with water (50 ml), dried over magnesium sulphate and evaporated under reduced pressure to give 1-trityl-3-methyl-1,2,4-triazole (19.0 g). Recrystallisation of a 2 g sample from toluene-hexane (1:1) gave pure material (1.32 g, m.p. 194-196° C.). NMR (CDCl3): δ 2.41(3H,s), 7.03-7.40(15H,m), 7.83(1H,s).

Workup

  1. washwashed with water (50 ml)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5b69a5b5a4c2495e91afd0e32ce65a9a
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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