Thiourea → HCID 13200303, compound

HRID 1903231Notes

Reaction equation

HRID 1903231 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[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:21]>C(O)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:2](=[S:21])[NH:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 132001832-Chloro-3-(4-fluorophenyl)quinoline

Product 1

HCID 13200303HCID 13200303, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-(p-fluorophenyl)quinoline (6.03 g., see Example 3) 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 then filtered. There was thus obtained as the solid residue 3-(p-fluorophenyl)quinolin-2-thione, m.p. 259°-262°.

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. filtrationfiltered

Sources & evidence

ORD record
ord-a6beca0cd12041e785a1bd338a2abd91
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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