Hydrochloric Acid → HCID 12319402, compound

HRID 1077329Notes

Reaction equation

HRID 1077329 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3([CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[O:10]2)=[CH:5][CH:4]=1.[H-].[Na+].C(S)C.Cl>CN(C)C=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3([CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[O:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 12319398HCID 12319398, compound

Product 1

HCID 12319402HCID 12319402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g. of 1,3-dihydro-3-p-methoxyphenyl-1'-methylspiro[isobenzofuran-1,4'-piperidine] (Example 12), 1.0 g. of a 57% sodium hydride dispersion, and dimethylformamide is stirred under nitrogen. To the stirring mixture is rapidly added 2.0 ml. of ethanethiol. The mixture is refluxed under nitrogen for 4 hours, cooled, poured into ice-water, and acidified with 1N hydrochloric acid. The product is collected, dried, and dissolved in boiling dimethyl sulfoxide, and the solution is filtered. Upon cooling small colorless crystals, m.p. 273° dec., separate.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureThe mixture is refluxed under nitrogen for 4 hours
  3. temperaturecooled
  4. customThe product is collected
  5. customdried
  6. dissolutiondissolved
  7. filtrationthe solution is filtered
  8. temperatureUpon cooling small colorless crystals, m.p. 273° dec.
  9. customseparate

Sources & evidence

ORD record
ord-49e0124893c142a8964ba1451ad2aa1d
Source dataset
uspto-grants-1976_05
Patent number
US03959475

Reaction notes

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