Toluene → HCID 67447079, compound

HRID 1876911Notes

Reaction equation

HRID 1876911 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[CH:14][N:15]([CH2:17]O)[CH:16]=2)=[CH:8][CH:7]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[ClH:3].[Cl:3][CH2:17][N:15]1[CH:16]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)[N:13]=[CH:14]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 67447090HCID 67447090, compound

Product 1

HCID 67447079HCID 67447079, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of thionyl chloride (18 mL) in anhydrous methylene chloride (180 mL) was added (4-(4-fluorophenyl)-1H-imidazol-1-yl)methanol (11.4 g, 59 mmol) portionwise at RT under nitrogen. The reaction mixture was stirred at RT for 3.5 hr before anhydrous toluene (90 mL) was added. The mixture was stirred at RT for 30 min. Concentration under reduced pressure gave 1-(chloromethyl)-4-(4-fluorophenyl)-1H-imidazole hydrochloride (14.5 g, 59 mmol, 100% yield) as a solid. MS found: (M+H)+=211.3.

Workup

  1. additionwas added
  2. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-652340960f8a4fc89505d7db4b468364
Source dataset
uspto-grants-2012_11
Patent number
US08309730B2

Reaction notes

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