Water → HCID 54188721, compound

HRID 905084Notes

Reaction equation

HRID 905084 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:8][C@@H:7]([O:9][CH:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH2:6][CH2:5][CH2:4]1.[S:25](Cl)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26].O>N1C=CC=CC=1>[S:25]([O:1][CH2:2][C@@H:3]1[O:8][C@@H:7]([O:9][CH:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH2:6][CH2:5][CH2:4]1)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 54319035HCID 54319035, compound

Product 1

HCID 54188721HCID 54188721, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5.10 g of 1-[trans-β-(6-hydroxymethyltetrahydropyran-2-yloxy)-2,4-dichlorophenethyl]imidazole in 40 ml of dry pyridine was stirred overnight at room temperature with 2.88 g of tosyl chloride. The reaction mixture was poured into water and extracted with diethyl ether. The ethereal extract was washed with aqueous sodium chloride and dried over anhydrous sodium sulphate, and the solvent was removed by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 20:20:1 by volume mixture of benzene, ethyl acetate and ethanol, to give 6.8 g of the title compound, as a colourless liquid.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ethereal extract
  3. washwas washed with aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. washeluted with a 20:20:1 by volume mixture of benzene, ethyl acetate and ethanol

Sources & evidence

ORD record
ord-e826ce18c97c4c77970577fc5a0cffdd
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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