Hydrochloric Acid → HCID 19826147, compound

HRID 1086510Notes

Reaction equation

HRID 1086510 reaction equation
Cl.[CH3:2][CH:3]1[S:16][C:7]2[N:8]([CH3:15])[C:9]3[C:14]([C:6]=2[C:5](=[O:17])[CH:4]1[CH2:18]N(C)C)=[CH:13][CH:12]=[CH:11][CH:10]=3.[CH3:22][C:23]1[NH:24][CH:25]=[CH:26][N:27]=1.Cl>O.O1CCCC1>[CH3:2][CH:3]1[S:16][C:7]2[N:8]([CH3:15])[C:9]3[C:14]([C:6]=2[C:5](=[O:17])[CH:4]1[CH2:18][N:24]1[CH:25]=[CH:26][N:27]=[C:23]1[CH3:22])=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 127492-MethylimidazoleHCID 19826167HCID 19826167, compound

Product 1

HCID 19826147HCID 19826147, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 g (0.062 mol) of 2,9-dimethyl-3-[(dimethylamino)methyl]-4-oxo-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole hydrochloride and 1.64 g (0.020 mol) of 2-methylimidazole in 30 ml of water is stirred under reflux under a nitrogen atmosphere for 16 hours. After the mixture is cooled, the precipitate formed is drained, washed with water and dried. The powder obtained is dissolved in 30 ml of tetrahydrofuran and the solution is treated with an ethereal solution of hydrochloric acid. The precipitate formed is drained, washed with ether, dried and recrystallized in ethanol. The two cis-trans isomers are obtained in a 50:50 ratio.

Workup

  1. temperatureunder reflux under a nitrogen atmosphere for 16 hours
  2. temperatureAfter the mixture is cooled
  3. customthe precipitate formed
  4. washwashed with water
  5. customdried
  6. customThe powder obtained
  7. customThe precipitate formed
  8. washwashed with ether
  9. customdried
  10. customrecrystallized in ethanol
  11. customThe two cis-trans isomers are obtained in a 50:50 ratio

Sources & evidence

ORD record
ord-22161048b0644651a875cf60ea209b0b
Source dataset
uspto-grants-1991_07
Patent number
US05030646

Reaction notes

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