Sodium Thiosulfate → HCID 19002956, compound

HRID 1728334Notes

Reaction equation

HRID 1728334 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 chroraatographed on a column of silica gel, eluting with ethyl acetate/n-hexane (1:1) to give 580 rag 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. washeluting with ethyl acetate/n-hexane (1:1)

Sources & evidence

ORD record
ord-56a50036d17848a6a9c6b31bea06df44
Source dataset
uspto-grants-1994_07
Patent number
US05326780

Reaction notes

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