Hydrochloric Acid → HCID 178488771, compound

HRID 1903716Notes

Reaction equation

HRID 1903716 reaction equation
[CH:1]([CH:3]([C:14]1[CH:21]=[CH:20][C:17]([O:18][CH3:19])=[CH:16][CH:15]=1)[C:4](=O)[C:5]1[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[CH:7][CH:6]=1)=O.[NH2:22][C:23]([NH2:25])=[S:24].Cl>C(O)C>[SH:24][C:23]1[N:25]=[C:4]([C:5]2[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[CH:7][CH:6]=2)[C:3]([C:14]2[CH:21]=[CH:20][C:17]([O:18][CH3:19])=[CH:16][CH:15]=2)=[CH:1][N:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 12679120HCID 12679120, compound

Product 1

HCID 178488771HCID 178488771, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of α-formyl desoxyanisoin (21.3 g, 75 mmole) and thiourea (9.75 g, 1.7 equiv) in 375 ml ethanol was treated with 3 N HCl (7.5 ml) and heated at reflux for 3.5 hours. The reaction mixture was concentrated on the rotary evaporator and the residue recrystallized from ethanol to give the title compound (11.6 g), m.p. 188°-191°. Infrared and H-NMR spectra were consistent with the assigned structure.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 hours
  3. concentrationThe reaction mixture was concentrated on the rotary evaporator
  4. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-30f75acff5bc400f901d41af688a1dd8
Source dataset
uspto-grants-1984_03
Patent number
US04438117

Reaction notes

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