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

HRID 2379132Notes

Reaction equation

HRID 2379132 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([C:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:12]2[CH:16]=[C:15]([CH2:17]O)[N:14]=[CH:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl.CN(C=O)C.CCCCCC>[Cl:3][CH2:17][C:15]1[N:14]=[CH:13][N:12]([C:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:16]=1

Participants

6

Reactant 2

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

Product 1

HCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleYield 93.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Thionyl chloride (0.82 g) was added over 1 min. to a stirred suspension of 1-(triphenylmethyl)-1H-imidazole-4-methanol (1.3 g) in a mixture of dichloromethane (50 ml) and DMF (1.0 ml) at 23°. The solution so obtained was stirred for 15 min. and extracted with 8% sodium bicarbonate solution (80 ml). The organic phase was washed with water (50 ml), dried and evaporated to give an oil which solidified. The solid was slurried in hexane and filtered to give the title compound (1.28 g), m.p. 139°-141°.

Workup

  1. customThe solution so obtained
  2. extractionextracted with 8% sodium bicarbonate solution (80 ml)
  3. washThe organic phase was washed with water (50 ml)
  4. customdried
  5. customevaporated
  6. customto give an oil which
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d2ce405fdb094333b8c911e4775d3c1f
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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