Boron Trichloride → HCID 22130250, compound

HRID 1416000Notes

Reaction equation

HRID 1416000 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

(2)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 addled 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 and 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. mp 84-86° C.

Workup

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

Sources & evidence

ORD record
ord-f30a24d544d943a4837291976e8460e0
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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