Diethyl Ether → HCID 22821723, compound

HRID 223175Notes

Reaction equation

HRID 223175 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C@@H:9]([CH2:12][C:13]3[NH:14][CH:15]=[CH:16][N:17]=3)[C@@H:10]([OH:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20][S:21][CH2:22]Cl.CCOCC>CN(C)C=O>[Cl:1][C:2]1[C:7]2[S:8][C@@H:9]([CH2:12][C:13]3[NH:17][CH:16]=[CH:15][N:14]=3)[C@@H:10]([O:11][CH2:20][S:21][CH3:22])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 22821721HCID 22821721, compound

Product 1

HCID 22821723HCID 22821723, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of cis-7-chloro-3-hydroxy-2,3-dihydro-2-(1'-imidazolylmethyl)benzo(b)thiophene (2.67 gms., 10 mmols) in dry dimethylformamide (30 ml.) at 0°-5° C., add sodium hydride (50% oil dispersion) (0.53 gms., 11 mmols) and stir for one hour at room temperature. Add chloromethyl methyl sulfide (1.06 gms., 11 mmols) and stir again for one hour at room temperature. Pour the reaction mixture into ether (500 ml.) and extract with three portions (500 ml. each) of water. Dry the ether solution over anhydrous magnesium sulfate and evaporate in vacuo. Chromatograph the resultant residue by high pressure liquid chromatography using two silica gel cartridges and eluting with ethyl acetate. Combine the like eluates as determined by thin layer chromatography and evaporate the combined residues to give cis-7-chloro-3-(methylthiomethoxy)-2,3-dihydro-2-(1'-imidazolylmethyl)benzo(b)-thiophene.

Workup

  1. extractionextract with three portions (500 ml
  2. dry with materialDry the ether solution over anhydrous magnesium sulfate
  3. customevaporate in vacuo
  4. washeluting with ethyl acetate
  5. customevaporate the combined residues

Sources & evidence

ORD record
ord-0bd17da7b7ac479e82636a68c759e75e
Source dataset
uspto-grants-1982_10
Patent number
US04352808

Reaction notes

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