Boron Trichloride → HCID 22130250, compound

HRID 1857704Notes

Reaction equation

HRID 1857704 reaction equation
[CH2:1]([N:4]1[C:8]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[C:7]([CH:17]([CH3:19])[CH3:18])[N:6]=[C:5]1[CH2:20]OCC1C=CC=CC=1)[CH:2]=[CH2:3].B(Cl)(Cl)[Cl:30].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([N:4]1[C:8]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[C:7]([CH:17]([CH3:19])[CH3:18])[N:6]=[C:5]1[CH2:20][Cl:30])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 22130396HCID 22130396, compound

Product 1

HCID 22130250HCID 22130250, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-40 °C

Procedure

In 5 ml of methylene chloride was dissolved 470 mg (1.13 mmol) of 1-allyl-2-benzyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazole (17g), with cooling to -40° C., 0.7 ml (1.36 mmol) of methylene chloride solution of boron trichloride (1.94 molar) was added with stirring, and the mixture was stirred for 30 minutes. To this reaction mixture, a saturated aqueous solution of sodium bicarbonate was added for neutralization, methylene chloride layer was washed with water arid dried over sodium sulfate. The solvent was concentrated under reduced pressure and the residue was fractionated by silica gel chromatography (ethyl acetate: methylene chloride=1:4). From the first fraction, 50 mg (yield 13%) of 1-allyl-2-chloromethyl-5-(3-chlorophenylthio)-4-isopropylimidazole (28a) was obtained as oil, and then, 155 mg (yield 43%) of Compound I-17 was obtained.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. washwas washed with water arid
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-97bf25d32eec408b8294bdd860b1c83d
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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