Ethanol → HCID 4086642, compound

HRID 1658676Notes

Reaction equation

HRID 1658676 reaction equation
C([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[S:10])=[CH:7][CH:6]=1)(=O)C.C(O)C.S(=O)(=O)(O)O>O>[NH2:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[S:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 12535530HCID 12535530, compound

Product 1

HCID 4086642HCID 4086642, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1-(4-Acetamidothiobenzoyl)piperidine (131.2 g, 0.5 mole), ethanol (500 ml), water (1 l) and concentrated sulphuric acid (125 ml) were mixed together and refluxed for 16 hours with stirring; nearly all the solid dissolved during the first hour. The reaction mixture was cooled to about 40°C and filtered quickly to remove any insoluble material. The filtrate was then made alkaline with 6N sodium hydroxide solution using external ice-cooling. The yellow crystalline solid was filtered off, washed with water and dried in vacuo at a temperature of under 50°C. Recrystallisation of the crude product (91 g; m.p. 162°-164°) by dissolving in 6 volumes of warm chloroform (about 546 ml) followed by adding 5 volumes of petroleum ether (b.p. 40°-60°) (about 455 ml) yielded yellow crystals (85 g; 77.3%), m.p. 164°-165°.

Workup

  1. temperaturerefluxed for 16 hours
  2. dissolutionnearly all the solid dissolved during the first hour
  3. filtrationfiltered quickly
  4. customto remove any insoluble material
  5. temperaturecooling
  6. filtrationThe yellow crystalline solid was filtered off
  7. washwashed with water
  8. customdried in vacuo at a temperature of under 50°C
  9. customRecrystallisation of the crude product (91 g; m.p. 162°-164°)
  10. dissolutionby dissolving in 6 volumes of warm chloroform (about 546 ml)
  11. additionby adding 5 volumes of petroleum ether (b.p. 40°-60°) (about 455 ml)
  12. customyielded yellow crystals (85 g; 77.3%), m.p. 164°-165°

Sources & evidence

ORD record
ord-1f948d93a6f041cf85ed2d01f840382f
Source dataset
uspto-grants-1976_06
Patent number
US03966397

Reaction notes

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