Thionyl Chloride → 2-Chloromethyl-1-methyl-4-phenyl-1H-imidazole

HRID 1474041Notes

Reaction equation

HRID 1474041 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH2:13]O.O=S(Cl)[Cl:17]>>[Cl:17][CH2:13][C:3]1[N:2]([CH3:1])[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 23076602(1-Methyl-4-phenyl-1H-imidazol-2-yl)-methanol

Product 1

HCID 591512282-Chloromethyl-1-methyl-4-phenyl-1H-imidazole

Procedure

To a solution of (1-Methyl-4-phenyl-1H-imidazol-2-yl)-methanol 5 (0.2 g, 0.097 mmol) was added SOCl2 (0.14 g, 0.121 mmol), and the mixture was stirred at room temperature overnight. The mixture was evaporated to afford 2-Chloromethyl-1-methyl-4-phenyl-1H-imidazole 6, which was used without purification. 1H NMR (400 MHz, DMSO-d6): δ8.24 (s, 1H), 7.87 (d, J=6.8 Hz, 2H), 7.54-7.49 (m, 2H), 7.43-7.41 (m, 1H), 5.24 (s, 2H), 3.89 (s, 3H).

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-9f55c1049cfe461da51221b4d8477f44
Source dataset
uspto-grants-2015_04
Patent number
US09018217B2

Reaction notes

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