Thiourea → HCID 13200300, compound

HRID 1903227Notes

Reaction equation

HRID 1903227 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.NC(N)=[S:22]>C(O)C>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:2](=[S:22])[NH:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:13][CH:14]=1)#[N:19]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 13200194HCID 13200194, compound

Product 1

HCID 13200300HCID 13200300, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-(p-cyanophenyl)quinoline (6.25 g., see Example 30) and thiourea (1.8 g.) in ethanol (30 ml.) was heated under reflux for 2 hr. The solution was allowed to cool to ambient temperature, the solid which precipitated was filtered off, dispersed in 1 M-sodium hydroxide solution (100 ml.) and the dispersion heated on a steam bath for 20 min. The mixture was acidified with 2 M-hydrochloric acid solution. The resulting mixture was filtered, the solid residue was stirred with hot ethanol (75 ml.) for 5 min., and the mixture was then filtered. There was thus obtained as the solid residue 3-(p-cyanophenyl)quinolin-2-thione, m.p. 284°-9°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. customthe solid which precipitated
  4. filtrationwas filtered off
  5. additiondispersed in 1 M-sodium hydroxide solution (100 ml.)
  6. temperaturethe dispersion heated on a steam bath for 20 min
  7. filtrationThe resulting mixture was filtered
  8. filtrationthe mixture was then filtered

Sources & evidence

ORD record
ord-50b05879f72740448e87c4ce20e54d5c
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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