Water → 1-Fluoroethvlbenzimidazole

HRID 2231237Notes

Reaction equation

HRID 2231237 reaction equation
O[CH:2]([C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:3].C(N(S(F)(F)[F:19])CC)C.O.[OH-].[Na+]>C(Cl)Cl>[F:19][CH:2]([C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 123472(Diethylamino)sulfur trifluorideHCID 2059221-(1H-1,3-benzodiazol-2-yl)ethan-1-ol

Product 1

HCID 538247831-FluoroethvlbenzimidazoleYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 3.24 g (0.02 mole) of 1-hydroxyethylbenzimidazole in 50 ml of methylene chloride was added to a solution of 2.44 ml (0.02 mole) of diethylaminosulfur trifluoride in 50 ml of methylene chloride cooled to -78° C. and under a nitrogen atmosphere. The reaction mixture was allowed to warm slowly to room temperature where it was stirred for 4 hours. The mixture was poured into water, the pH adjusted to 8 with aqueous sodium hydroxide solution and the organic layer separated and dried. Removal of the solvent gave 1.25 g of a brown oil which was chromatographed on 100 g of silica gel using 5% methanol chloroform as the eluent, 845 mg.

Workup

  1. temperatureto warm slowly to room temperature where it
  2. customthe organic layer separated
  3. customdried
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-dd2fc4b3387d4ce39a2ef7faa0ce19b6
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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