Sodium Thiosulfate → HCID 19002956, compound

HRID 2259238Notes

Reaction equation

HRID 2259238 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14](SC2C=CC=CC=2)=[C:13]([CH:22]([CH3:24])[CH3:23])[N:12]=[C:11]1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:27]1[CH:32]=[CH:31][CH:30]=[C:29](C(OO)=O)[CH:28]=1.[S:37]([O-:41])([O-])(=[O:39])=S.[Na+].[Na+].[Na]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([S:37]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:41])=[O:39])=[C:13]([CH:22]([CH3:23])[CH3:24])[N:12]=[C:11]1[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 475887HCID 475887, compoundHCID 5360545Sodium

Product 1

HCID 19002956HCID 19002956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g of 1-benzyloxymethyl-4-isopropyl-2-methyl-5-phenylthio-imidazole (2.8 mmol) in 40 ml of methylene chloride is added 1.84 g of m-chloroperbenzoic acid (10.7 mmol) under ice cooling, and the resultant mixture is stirred at room temperature. Six hours later, the reaction mixture is mixed with aqueous sodium thiosulfate and aqueous sodium hydrogenecarbonate and extracted with methylene chloride. The extract is washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is chromatographed on a column of silica gel, eluting with ethyl acetate/n-hexane (1:1) to give 580 mg of the objective 1-benzyloxymethyl-4-isopropyl-2-methyl-5-phenylsulfonyl-imidazole as crystals melting at mp. 116°-117° C. Yield, 53%.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on a column of silica gel
  7. washeluting with ethyl acetate/n-hexane (1:1)

Sources & evidence

ORD record
ord-345e9d17511647d6a4392aa6b633765d
Source dataset
uspto-grants-1995_12
Patent number
US05472965

Reaction notes

Loading…