Hydrochloric Acid → HCID 86734370, compound

HRID 1414531Notes

Reaction equation

HRID 1414531 reaction equation
C(S)C.[H-].[Na+].C[O:7][C:8]1[C:13]2[S:14][C:15]3[C:20]([C:21]4([CH2:26][CH2:25][N:24]([CH2:27][CH:28]=[CH2:29])[CH2:23][CH2:22]4)[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3.Cl>CN(C)C=O.O>[OH:7][C:8]1[C:13]2[S:14][C:15]3[C:20]([C:21]4([CH2:26][CH2:25][N:24]([CH2:27][CH:28]=[CH2:29])[CH2:23][CH2:22]4)[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 86734371HCID 86734371, compound

Product 1

HCID 86734370HCID 86734370, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of ethanethiol (1.49 ml.) in dry dimethylformamide (30 ml.) in an atmosphere of nitrogen is treated portionwise with sodium hydride (800 mg. of a 60% dispersion in mineral oil), with stirring at 20°-25° C. After 15 mins. the internal temperature is raised to 100° C. and the 4-methoxy-1'-allylthioxanthene-9-spiro-4'-piperidine (1.685 g.) is added in one portion. The solution is heated at 100° C. for 45 mins., cooled to ambient temperature, poured into water (300 ml.), acidified with concentrated HCl, the mixture filtered and the filtrate rebasified with solid sodium carbonate and extracted three times with ethyl acetate. The combined ethyl acetate extracts are washed with water, dried over MgSO4 and then evaporated, to give 4-hydroxy-1'-allylthioxanthene-9-spiro-4'-piperidine m.p. 224° C. on recrystallisation from methanol/dimethylformamide/water.

Workup

  1. temperatureThe solution is heated at 100° C. for 45 mins
  2. temperature, cooled to ambient temperature
  3. filtrationthe mixture filtered
  4. extractionextracted three times with ethyl acetate
  5. washThe combined ethyl acetate extracts are washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-cdf86696bc984ae8b6e7dcf8014c551a
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

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