Hydrochloric Acid → 2-[2-(1-aminocyclohexyl)ethyl]-8H-indeno[1,2-d]thiazole

HRID 356117Notes

Reaction equation

HRID 356117 reaction equation
[N+:1]([C:4]1([CH2:10][CH2:11][C:12]2[S:13][C:14]3[CH2:23][C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:15]=3[N:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([O-])=O.O.S(=O)(=O)(O)O.Cl>CO.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].[Fe]>[NH2:1][C:4]1([CH2:10][CH2:11][C:12]2[S:13][C:14]3[CH2:23][C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:15]=3[N:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 189410532-[2-(1-Nitrocyclohexyl)ethyl]-8H-indeno[1,2-d]thiazole

Product 1

HCID 189410292-[2-(1-aminocyclohexyl)ethyl]-8H-indeno[1,2-d]thiazoleYield 14.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 62662Ferrous sulfate heptahydrateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 910 mg of 2-[2-(1-nitrocyclohexyl)ethyl]-8H-indeno[1,2-d]thiazole in 10 ml of methanol were added 390 mg of iron(II) sulfate heptahydrate, 290 mg of iron reduced, 30 ml of water, and 1.5 g of concentrated sulfuric acid successively, followed by heating under reflux for 2 hours. The reaction mixture was poured into 1N hydrochloric acid, followed by extraction with ethyl acetate to remove unreacted starting materials. The aqueous layer was then neutralized, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, whereby 120 mg of yellow 2-[2-(1-aminocyclohexyl)ethyl]-8H-indeno[1,2-d]thiazole was obtained as a free base. Fumaric acid was added to the resulting compound in ethanol to cause crystallization, and the crystals were recrystallized to give a fumarate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. customto remove unreacted
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cc3fae23d7084c4a8ec7654fb93dbfc5
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Reaction notes

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