Hydrazine hydrate (1:1) → HCID 19605190, compound

HRID 1603503Notes

Reaction equation

HRID 1603503 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][C:10]2[N:11]3[CH:18]=[N:17][CH:16]=[C:12]3[S:13][C:14]=2[CH3:15])C(=O)C2=CC=CC=C12>C(O)C>[NH2:8][CH2:9][C:10]1[N:11]2[CH:18]=[N:17][CH:16]=[C:12]2[S:13][C:14]=1[CH3:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19605050HCID 19605050, compound

Product 1

HCID 19605190HCID 19605190, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.42 ml portion of hydrazine hydrate was added to 30 ml of a dry ethanol solution containing 1.7 g of 3-phthalimidomethyl-2-methylimidazo[5,1-b]thiazole, and the mixture was then heated under reflux for 2 hours. The reaction solution was cooled on ice, and the resulting crystal was filtered and then washed with a small amount of cold methanol. The filtrate was concentrated under reduced pressure, and to the resulting residue, dichloromethane was added. The solution was extracted with 1N hydrochloric acid, and the extract was then alkalified with a 1N aqueous potassium hydroxide solution. The organic layer extracted from the aqueous layer with dichloromethane was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was evaporated under reduced pressure to obtain 820 mg of 3-aminomethyl-2-methylimidazo[5,1-b]thiazole as a green powder.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction solution was cooled on ice
  4. filtrationthe resulting crystal was filtered
  5. washwashed with a small amount of cold methanol
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionto the resulting residue, dichloromethane was added
  8. extractionThe solution was extracted with 1N hydrochloric acid
  9. extractionThe organic layer extracted from the aqueous layer with dichloromethane
  10. dry with materialwas dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a8595310e18c43148142275f2cc5090a
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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