Hydrochloric Acid → HCID 15700630, compound

HRID 236783Notes

Reaction equation

HRID 236783 reaction equation
[CH:1]([NH:3][C:4]1(NC)[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)=O.Cl.[OH-].[Na+].C(Cl)Cl>O>[CH3:1][NH:3][C:4]1[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 213158793-Formamido-3-methylamino-2-phenyl-benzo(b)thiophene

Product 1

HCID 15700630HCID 15700630, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34.2 g (0.13 mol) of 3-formamido-3-methylamino-2-phenyl-benzo(b)thiophene are refluxed with stirring for 4 hours with 300 milliliters of HCl at 25%. After cooling, it is diluted in water, made alkaline by sodium hydroxide solution and stirred with CH2Cl2. After the organic phase has been extracted several times 2 N NaOH 7.4 g (26% of theory) of 2-phenyl-thioindole are isolated. By evaporating the solution of CH2Cl2 dried over K2CO3, the 3-methylamino-2-phenyl-benzo(b)thiophene is obtained in the form of a crude oily product. It is dissolved in a little CHCl3 and converted into the hydrochloride by hydrochloric gas: 20.2 g (57% of theory) of colourless prisms in a mixture of ethanol and ether, decomposition from 198° C. (in a sealed tube).

Workup

  1. temperatureAfter cooling
  2. extractionAfter the organic phase has been extracted several times 2 N NaOH 7.4 g (26% of theory) of 2-phenyl-thioindole
  3. customare isolated
  4. customBy evaporating the solution of CH2Cl2
  5. dry with materialdried over K2CO3

Sources & evidence

ORD record
ord-0b5baca1e11d4d3b93afeb1b3a3fbcc3
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Reaction notes

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