Sodium hydride → HCID 13361843, compound

HRID 2413484Notes

Reaction equation

HRID 2413484 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8][CH2:7]2.[H][H].CS(O[CH2:21][CH:22]1[CH2:26][O:25][C:24]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[Cl:40])([CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[O:23]1)(=O)=O>CS(C)=O>[Cl:40][C:34]1[CH:35]=[C:36]([Cl:39])[CH:37]=[CH:38][C:33]=1[C:24]1([CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[O:23][CH:22]([CH2:21][O:3][C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][NH:9][CH2:8][CH2:7]3)[CH2:26][O:25]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 266981,2,3,4-Tetrahydroisoquinolin-6-olHCID 11177254HCID 11177254, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13361843HCID 13361843, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

0.55 g of sodium hydride (50% suspension in oil) is added to a solution of 1.50 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline in 30 ml of dimethyl sulfoxide, and the mixture is stirred at 50° C. until evolution of hydrogen has finished. 4.07 g of (2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl methanesulfonate are added and the mixture is stirred at 80° C. for 5 hours. The solvent is removed under oil pump vacuum, the residue is taken up with a mixture of 50 ml of water and 50 ml of methylene chloride, and the organic phase is extracted twice more by shaking with water, dried and evaporated in a rotary evaporator. The residue is chromatographed on silica gel using methanol as the mobile phase. 2.45 g of colorless oil (53% of theory), which gradually crystallizes, are obtained. Melting point 143°-145° C.

Workup

  1. customThe solvent is removed under oil pump vacuum
  2. additionthe residue is taken up with a mixture of 50 ml of water and 50 ml of methylene chloride
  3. extractionthe organic phase is extracted twice more
  4. stirringby shaking with water
  5. customdried
  6. customevaporated in a rotary evaporator
  7. customThe residue is chromatographed on silica gel
  8. custom2.45 g of colorless oil (53% of theory), which gradually crystallizes
  9. customare obtained

Sources & evidence

ORD record
ord-7bd862e697844a2b983466695df3ec1d
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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