N,N-Diethylaniline → 2-Chloro-5-fluoro-1-methyl-1H-benzimidazole

HRID 474174Notes

Reaction equation

HRID 474174 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH3:10])[C:7](=O)[NH:8][C:4]=2[CH:3]=1.CCN(C1C=CC=CC=1)CC.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:7]1[N:6]([CH3:10])[C:5]2[CH:11]=[CH:12][C:2]([F:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 220286845-Fluoro-1-methyl-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 219858282-Chloro-5-fluoro-1-methyl-1H-benzimidazole

Procedure

3.9 g 5-fluoro-1-methyl-1,3-dihydro-benzimidazol-2-one are suspended in 80 ml phosphorus oxychloride and the reaction mixture is stirred for 2 hours at reflux temperature. 50 ml diethylaniline are added. The reaction mixture is stirred for a further 10 minutes at reflux temperature and slowly combined with ice water. The product is extracted with dichloromethane and purified by chromatography (silica gel, cyclohexane, methylene chloride/acetone 20/1). 1.4 g product are obtained as a solid. M.p=138-141° C.

Workup

  1. temperatureat reflux temperature
  2. stirringThe reaction mixture is stirred for a further 10 minutes
  3. temperatureat reflux temperature
  4. extractionThe product is extracted with dichloromethane
  5. custompurified by chromatography (silica gel, cyclohexane, methylene chloride/acetone 20/1)

Sources & evidence

ORD record
ord-101e2bec51394d31bc9882cc6203f34d
Source dataset
uspto-grants-2014_01
Patent number
US08637519B2

Reaction notes

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