Thionyl Chloride → HCID 178514949, compound

HRID 1076713Notes

Reaction equation

HRID 1076713 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([OH:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1>C(Cl)(Cl)Cl>[Cl:3][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([OH:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178520828HCID 178520828, compound

Product 1

HCID 178514949HCID 178514949, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionylchloride (1.53 ml.) was added dropwise to a stirred cooled suspension of 2-(3-hydroxypropylamino)-3-phenyl-3H-indol-3-ol (3 g.) in chloroform (25 ml.). On completion of the addition the reaction was allowed to warm to room temperature and then heated under reflux for 45 minutes. The solvent and excess thionyl chloride were removed under reduced pressure and the resulting product crystallised from isopropanol-ether to give the title compound as its hydrochloride salt (2.72 g.). After two recrystallisations from isopropanol-ether the hydrochloride had a m.p. 210°-212°C. (Found C, 60.8; H. 5.6; N, 8.3. C17H17ClN20HCl requires C, 60.5; H, 5.4; N 8.3%).

Workup

  1. temperaturecooled
  2. additionOn completion of the addition the reaction
  3. temperatureheated
  4. temperatureunder reflux for 45 minutes
  5. customThe solvent and excess thionyl chloride were removed under reduced pressure
  6. customthe resulting product crystallised from isopropanol-ether

Sources & evidence

ORD record
ord-8f6710b7b2e74269af44a2a8ee29aebb
Source dataset
uspto-grants-1976_05
Patent number
US03957819

Reaction notes

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