Thionyl Chloride → 4-(Chloromethyl)-1-trityl-1H-imidazole

HRID 1739007Notes

Reaction equation

HRID 1739007 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.S(Cl)([Cl:29])=O>C(Cl)(Cl)Cl>[Cl:29][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Product 1

HCID 27631764-(Chloromethyl)-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

The product from Step F is dissolved in chloroform and cooled to 0° C. under nitrogen. Thionyl chloride (molar equivalent) is added slowly via syringe. The reaction is stirred for 30 min, and extracted with sodium bicarbonate solution. The organic phase is dried over magnesium sulfate, filtered and concentrated to provide the title compound.

Workup

  1. extractionextracted with sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f1a72b3a6204b4e95aa7fb5476a5d39
Source dataset
uspto-grants-1999_10
Patent number
US05965578

Reaction notes

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