Hydrochloric Acid → HCID 18941099, compound

HRID 356119Notes

Reaction equation

HRID 356119 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]2[S:8][C:9]3[CH2:18][C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:10]=3[N:11]=2)[CH2:4][C:3]1=O.Cl.CO>O1CCCC1>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:7]2[S:8][C:9]3[CH2:18][C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:10]=3[N:11]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18941014HCID 18941014, compound

Product 1

HCID 18941099HCID 18941099, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.11 g of 2-(1-methyl-2-oxo-4-pyrrolidinyl)-8H-indeno[1,2-d]thiazole in 4 ml of tetrahydrofuran, a 1.6 ml of a 1M solution of a borane-tetrahydrofuran complex in tetrahydrofuran was added, followed by heating under reflux for 2 hours. After cooling, a mixed solution of 10 ml of concentrated hydrochloric acid and 10 ml of methanol was added to the reaction mixture, followed by heating under reflux for 1.5 hours. The solvent was evaporated, and ethyl acetate and water were added to the resulting residue, followed by extraction with 1N hydrochloric acid. The aqueous layer was neutralized with sodium bicarbonate, followed by extraction with chloroform and drying over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was subjected to silica gel column chromatography, whereby 0.04 g of 2-(1-methyl-3-pyrrolidinyl)-8H-indeno[1,2-d]thiazole was obtained from the fraction eluted with chloroform-methanol-29% aqueous ammonia (300:10:1). The product was dissolved in methanol. Fumaric acid was added to the resulting solution, followed by crystallization from acetone to give a fumarate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperatureunder reflux for 1.5 hours
  6. customThe solvent was evaporated
  7. additionethyl acetate and water were added to the resulting residue
  8. extractionfollowed by extraction with 1N hydrochloric acid
  9. extractionfollowed by extraction with chloroform
  10. dry with materialdrying over anhydrous magnesium sulfate
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b9dc485adcac4943a5c79b6ef8857175
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Reaction notes

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