Thionyl Chloride → HCID 67324203, compound

HRID 1397390Notes

Reaction equation

HRID 1397390 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7]O)=[CH:5][N:4]=[C:3]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O=S(Cl)[Cl:17]>>[ClH:17].[Cl:17][CH2:7][C:6]1[N:2]([CH3:1])[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][CH:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 320833HCID 320833, compound

Product 1

HCID 67324203HCID 67324203, compoundYield 86%

Procedure

A solution of (1-methyl-2-phenyl-1H-imidazol-5-yl)methanol (0.600 g, 3.19 mmol) in dry SOCl2 (11 mL) was refluxed at 80° C. for 1 h. The reaction mixture was concentrated under reduced pressure and the residue was co-evaporated with CH2Cl2, and then triturated with diethyl ether, filtered and dried under suction to afford 5-(chloromethyl)-1-methyl-2-phenyl-1H-imidazole hydrochloride (0.67 g, yield 86%) as a white solid. 1H NMR (300 MHz, MeOD) δ 7.79-7.79 (m, 6H), 4.98 (s, 2H), 3.93 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customtriturated with diethyl ether
  3. filtrationfiltered
  4. customdried under suction

Sources & evidence

ORD record
ord-4427e338a04041d2aad81906141105d0
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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