Diethyl Ether → 3-Phenylquinolin-2-thione

HRID 1903216Notes

Reaction equation

HRID 1903216 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[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:20].C(OCC)C>C(O)C>[C:12]1([C:11]2[C:2](=[S:20])[NH:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2723790ThioureaHCID 42560782-Chloro-3-phenylquinoline

Product 1

HCID 132002063-Phenylquinolin-2-thione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-phenylquinoline (3.4 g.) and thiourea (1.2 g.) in ethanol (20 ml.) was refluxed for one hour. The solution was allowed to cool to ambient temperature and diethyl ether (10 ml.) was added. The solid which precipitated was filtered off, dispersed in M-sodium hydroxide (70 ml.), and heated on a steam bath for 2 hr. The reaction mixture was acidified with 2 M-hydrochloric acid. The resulting mixture was filtered, and the solid residue was stirred with hot ethanol (50 ml.) and filtered. There was thus obtained as the solid residue 3-phenylquinolin-2-thione, m.p. 242°-4°.

Workup

  1. temperaturewas refluxed for one hour
  2. customThe solid which precipitated
  3. filtrationwas filtered off
  4. additiondispersed in M-sodium hydroxide (70 ml.)
  5. temperatureheated on a steam bath for 2 hr
  6. filtrationThe resulting mixture was filtered
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7477dd82260441f6b87c6158416abdc1
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

Loading…