Sodium Hydroxide → HCID 15166265, compound

HRID 357562Notes

Reaction equation

HRID 357562 reaction equation
[O:1]([CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:17]O)[C:12]=1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH-].[Na+].[SH:26][C:27]1[NH:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>C(O)C.ClCCl>[O:1]([CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][S:26][C:27]2[NH:31][C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[N:28]=2)[C:12]=1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 19600530HCID 19600530, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 15166265HCID 15166265, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture comprising 1.0 g of [4-(2-phenoxyethoxy)-3-methylpyridine-2-yl]methanol, 0.60 ml of thionyl chloride and 12 ml of dichloromethane was kept at 40° C. for 60 minutes to carry out the reaction. The reaction mixture was distilled to remove the solvent. Thus, a brown syrupy residue was obtained. 50 ml of ethanol, 0.70 g of sodium hydroxide and 1.2 g of 2-mercaptobenzimidazole were added to the residue. The obtained mixture was heated at 70° C. for two hours and distilled to remove the ethanol. The obtained residue was chromatographed over a silica gel column and eluted with 30% ethyl acetate in hexane and then with ethyl acetate to obtain 1.2 g of the title compound as a white solid.

Workup

  1. customthe reaction
  2. distillationThe reaction mixture was distilled
  3. customto remove the solvent
  4. customThus, a brown syrupy residue was obtained
  5. distillationdistilled
  6. customto remove the ethanol
  7. customThe obtained residue was chromatographed over a silica gel column
  8. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9b4b973f1658495e895cb8fb178d3f51
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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