Diazomethane → HCID 10243171, compound

HRID 1707424Notes

Reaction equation

HRID 1707424 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][S:8][C:9]2[N:13]=[CH:12][NH:11][N:10]=2)=[CH:5][CH:4]=1.[N+](=[CH2:18])=[N-]>CO.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[N:10]([CH3:18])[N:11]=[CH:12][N:13]=2)=[CH:14][CH:15]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[N:13]=[CH:12][N:11]([CH3:18])[N:10]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 178491706HCID 178491706, compound

Product 2

HCID 10243171HCID 10243171, compoundYield 49%HCID 10444086HCID 10444086, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-p-methoxybenzylthio-1,2,4-triazole (10.0 g: 45.2 mMol.) in methanol (100 ml) is added under ice cooling a solution of diazomethane in ether (prepared from 15 g of N-nitrosomethylurea), and the mixture is stirred for 1 hour. The reaction mixture is concentrated and purified by Lobar column chromatography (toluene: ethyl acetate=1:2 to 1:3) to give 3-p-methoxybenzylthio-2-methyl-1,2,4-triazole [5.17 g: NMR δ(CDCl3) ppm: 3.63(s, 3H), 3.79(s, 3H), 4.34(s, 2H), 6.80-6.84, 7.19-7.24(A2B2, 4H), 7.88(s, 1H). IR ν(CHCl3) cm-1 : 1611, 1511, 1476, 1464, 1440, 1360, 1302. Yield: 49%] and 3-p-methoxybenzylthio-1-methyl-1,2,4-triazole [3.60 g: NMR δ(CDCl3) ppm: 3.78(s, 3H), 3.87(s, 3H), 4.31(s, 2H), 6.80-6.85, 7.30-7.34(A2B2, 4H), 7.99(s, 1H). IR ν(CHCl3) cm-1 : 1612, 1512, 1465, 1440, 1421, 1356, 1302. Yield: 34%].

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified by Lobar column chromatography (toluene: ethyl acetate=1:2 to 1:3)

Sources & evidence

ORD record
ord-5ebe5a29e3e546bdbc1df55fcc852d9c
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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