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

HRID 2422379Notes

Reaction equation

HRID 2422379 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>ClCCl>[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-imidazoleYield 114.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-hydroxymethyl-1-tritylimidazole (6.13 g, 18 mmol) in dichloromethane (75 mL), cooled using an ice/water, was added dropwise thionyl chloride (5.0 g, 42 mmol) over 6 min. The ice/water bath was removed and the reaction was stirred for an additional 30 min. The DCM and SOCl2 were removed under reduced pressure. The resulting solid was triturated with diisopropyl ether (200 mL), collected by filtration and dried in vacuo to give 7.37 g (>100%) of 83% pure 4-(chloromethyl)-1-trityl-1H-imidazole; retention time, 7.33 min.; column: YMC ODS-A (3 μm, 50×4.6 mm); gradient: 10% to 100% B in A over 10 min. at 1.25 mL/min. Solvent A: 0.1% TFA in water, Solvent B: 0.1% TFA in AcCN. LC/MS: ESI (M+H)+=359.2.

Workup

  1. temperaturecooled
  2. customThe ice/water bath was removed
  3. customThe DCM and SOCl2 were removed under reduced pressure
  4. customThe resulting solid was triturated with diisopropyl ether (200 mL)
  5. filtrationcollected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-42e2e2ef73c44a9b87b6ae75bac288e9
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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