Hydrochloric Acid → HCID 19736736, compound

HRID 326310Notes

Reaction equation

HRID 326310 reaction equation
C[O:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([S:17][C:7]=2[CH:6]=[C:5]([O:19]C)[CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3.Cl.N1C=CC=CC=1.Cl>>[OH:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([S:17][C:7]=2[CH:6]=[C:5]([OH:19])[CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 19736704HCID 19736704, compound

Product 1

HCID 19736736HCID 19736736, compoundYield 96.5%

Procedure

A mixture of 5,7-Dimethoxyspiro[2H-1-benzothiin -2,1'-cyclohexan]-4(3H)-one (prepared in Preparation 78) (0.526 g, 1.80 mmol) and pyridine hydrochloride (4 g, 34.6 mmol) is heated at 205°-210° C. for 50 minutes with stirring under nitrogen gas. After cooling, dilute HCl is added to the mixture. The mixture is extracted with diethyl ether. The extract is washed with saturated brine, dried, and the solvent is removed. The residue is placed on a silica gel column and eluted with a mixture of ethyl acetate and dichloromethane (1:9) to obtain the title compound as a crystalline solid (0.459 g, 96%). Recrystallization from diethyl ether gives a product having a melting point of 160°-162° C.

Workup

  1. temperatureis heated at 205°-210° C. for 50 minutes
  2. temperatureAfter cooling
  3. extractionThe mixture is extracted with diethyl ether
  4. washThe extract is washed with saturated brine
  5. customdried
  6. customthe solvent is removed
  7. washeluted with a mixture of ethyl acetate and dichloromethane (1:9)

Sources & evidence

ORD record
ord-fe4de199db474f80b27b068e8f6ac3ae
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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