1H-Indole-3-thiol → HCID 14053217, compound

HRID 1252504Notes

Reaction equation

HRID 1252504 reaction equation
[OH-].[Na+].[SH:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.Cl[CH2:15][C:16]1[CH:21]=[C:20]([N:22]([CH3:24])[CH3:23])[CH:19]=[CH:18][N:17]=1>C(O)C.O>[CH3:23][N:22]([CH3:24])[C:20]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:15][S:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[CH:21]=1

Participants

6

Reactant 3

HCID 102001H-Indole-3-thiolHCID 14798Sodium Hydroxide2×HCID 20140063HCID 20140063, compound

Product 1

HCID 14053217HCID 14053217, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of S-(3-indolyl)isothioronium iodide (180 mg, 0.75 mmol) of the formula ##STR37## in ethanol (5 ml) was added a 2N aqueous sodium hydroxide solution (0.86 ml) under ice-cooling, and the mixture obtained was stirred at room temperature for 1 hour. The resultant reaction solution containing 3-mercapto-indole so formed was then admixed with 2-chloromethyl-4-dimethylaminopyridine hydrochloride (118 mg, 0.75 mmol), followed by stirring the mixture at room temperature for 1 hour. The resulting reaction was made strongly alkaline with a 2N aqueous sodium hydroxide solution (1.0 ml) and then diluted with water (20 ml) to precipitate crystals, affording the titled compound (130 mg) after filtration.

Workup

  1. temperaturecooling
  2. customthe mixture obtained
  3. customThe resultant reaction solution
  4. customso formed
  5. stirringby stirring the mixture at room temperature for 1 hour
  6. customThe resulting reaction
  7. customto precipitate crystals

Sources & evidence

ORD record
ord-b0d2188dfd7740a7b59c6061db377290
Source dataset
uspto-grants-1988_05
Patent number
US04743609

Reaction notes

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