Diazomethane → HCID 10082838, compound

HRID 1707427Notes

Reaction equation

HRID 1707427 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][S:8][C:9]2[NH:13][N:12]=[N: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]=[N:11][N:12]([CH3:18])[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]([CH3:18])[N:12]=[N:11][N:10]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 178491711HCID 178491711, compound

Product 2

HCID 785696HCID 785696, compoundYield 36%HCID 10082838HCID 10082838, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-p-methoxybenzylthiotetrazole (7.00 g: 31.5 mMol.) in methanol (150 ml) is added under ice cooling a solution of diazomethane in ether (produced from 14 g of N-nitrosomethylurea), and the mixture is stirred for 1 hour and then concentrated. The residue is purified by Lobar column chromatography (toluene: ethyl acetate=5:1) to give 5-p-methoxybenzylthio-2-methyltetrazole [4.86 g: NMR δ(CDCl3) ppm: 3.78(s, 3H), 4.29(s, 3H), 4.38(s; 2H), 6.81-6.85, 7.30-7.34 (A2B2, 4H). IR ν(CHCl3) cm-1 : 1611, 1512, 1390, 1324, 1303. colorless oil. Yield: 65%] and 5-p-methoxybenzylthio-1-methyltetrazole [2.71 g: NMR δ(CDCl3) ppm: 3.79(s, 3H), 3.80(s, 3H), 4.49(s, 2H), 6.82-6.86, 7.27-7.31(A2B2, 4H). IR ν(CHCl3) cm-1 : 1613, 1513, 1465, 1305. colorless crystals. Yield: 36%].

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by Lobar column chromatography (toluene: ethyl acetate=5:1)

Sources & evidence

ORD record
ord-cbe858b442e7435eb32b0f6f77df083b
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

Loading…