1,1-Dichloroethane → 2-(1-Chloro-ethyl)-1H-benzoimidazole

HRID 253464Notes

Reaction equation

HRID 253464 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10](O)[CH3:11].[Cl:13]C(Cl)C.S(Cl)(Cl)=O>>[Cl:13][CH:10]([C:2]1[NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=1)[CH3:11]

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 24386Thionyl ChlorideHCID 2059221-(1H-1,3-benzodiazol-2-yl)ethan-1-ol

Product 1

HCID 43472862-(1-Chloro-ethyl)-1H-benzoimidazole

Procedure

1-(1H-Benzimidazol-2-yl)-ethanol (146) (1.00 g, 6.16 mmol) was suspended in dichloro ethane (50 mL, 800 mmol). Thionyl chloride (4.00 mL, 54.8 mmol) was added dropwise and the reaction was stirred at room temperature and then heated to 60° C. for 6 hours. After cooling to room temperature the reaction was evaporated to dryness under reduced pressure. The obtained solid was washed with ethyl acetate. The powder was suspended in ethyl acetate and washed with saturated sodium bicarbonate solution and brine. The organic portion was dried over anhydrous sodium sulfate and concentrated. The obtained off-white solid was used without further purification (147, 0.864 g, 76%). MS (ESI) [M+H+]+=181.2.

Workup

  1. temperatureheated to 60° C. for 6 hours
  2. temperatureAfter cooling to room temperature the reaction
  3. customwas evaporated to dryness under reduced pressure
  4. washThe obtained solid was washed with ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe obtained off-white solid was used without further purification (147, 0.864 g, 76%)

Sources & evidence

ORD record
ord-3152bccee5844d5da8d704d660614213
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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