Thionyl Chloride → HCID 178515062, compound

HRID 1076710Notes

Reaction equation

HRID 1076710 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2([OH:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]2[NH:21][CH2:22][CH2:23][CH2:24]O)[CH:9]=[CH:10][CH:11]=1>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2([OH:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]2[NH:21][CH2:22][CH2:23][CH2:24][Cl:3])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178520830HCID 178520830, compound

Product 1

HCID 178515062HCID 178515062, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionylchloride (2.2 g., 1.36 ml.) was added dropwise to a stirred suspension of 3-(m-chlorophenyl)-2-(3-hydroxypropylamino)-3H-indol-3-ol (3.16 g.) in chloroform (25ml.) at 0°C. The reaction mixture was heated under reflux for 45 minutes. the mixture was then cooled and the chloroform evaporated off at reduced pressure. Toluene (25 ml.) was added to the residue and after evaporation the procedure was repeated with a second quantity of toluene. The residue was then dissolved in the minimum quantity of isopropyl alcohol and a small quantity of ether was added to give the title compound as the hydrochloride, colourless rhombs (2.20 g.), m.p. 199° to 203°C.(decomp.). (Found C, 55.15; H, 4.6; N, 7.5. C17H16N2Cl2O2HCl requires C, 54.9; H, 4.6; N, 7.5%)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperaturethe mixture was then cooled
  4. customthe chloroform evaporated off at reduced pressure
  5. additionToluene (25 ml.) was added to the residue
  6. customafter evaporation the procedure
  7. dissolutionThe residue was then dissolved in the minimum quantity of isopropyl alcohol
  8. additiona small quantity of ether was added

Sources & evidence

ORD record
ord-14cac7b8d87c46109184d5cf996d5cdd
Source dataset
uspto-grants-1976_05
Patent number
US03957819

Reaction notes

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