Dimethylformamide → 4-(Chloromethyl)-5-methyl-1-trityl-1H-imidazole

HRID 621195Notes

Reaction equation

HRID 621195 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[N:10]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[N:8][C:7]=1[CH2:30]O.CN(C=O)C>ClCCl>[Cl:3][CH2:30][C:7]1[N:8]=[CH:9][N:10]([C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[CH3:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11544901(5-Methyl-1-trityl-1H-imidazol-4-yl)methanol

Product 1

HCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of thionyl chloride (1.3 ml) in dry dichloromethane (10 ml) was added over 5 min. to a stirred suspension of 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-methanol (5.0 g) in a mixture of dichloromethane (100 ml) and dry DMF (2 ml) at 0°. The mixture was stirred at 0° for 30 min. and washed consecutively with 8% sodium bicarbonate (2×50 ml), water (50 ml), dried and evaporated in vacuo below 40° to give an oil (5 g). This was dissolved in ether (100 ml) and the resulting solution was filtered through a pad of silica which was further eluted with ether (2×100 ml). The combined filtrates were evaporated below 40° to give a foam which was triturated with cold hexane and filtered to give the title compound (4.2 g) as a solid, m.p. 133°-135°.

Workup

  1. washwashed consecutively with 8% sodium bicarbonate (2×50 ml), water (50 ml)
  2. customdried
  3. customevaporated in vacuo below 40°

Sources & evidence

ORD record
ord-009cc045daf1469f8f52efd3f09183c3
Source dataset
uspto-grants-1989_04
Patent number
US04822881

Reaction notes

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