Hydrazine → 2-Aminomethyl-3-methylimidazo[5,1-b]thiazole

HRID 1603441Notes

Reaction equation

HRID 1603441 reaction equation
NN.C1(=O)[N:7]([CH2:8][C:9]2[S:13][C:12]3=[CH:14][N:15]=[CH:16][N:11]3[C:10]=2[CH3:17])C(=O)C2=CC=CC=C12>CO>[NH2:7][CH2:8][C:9]1[S:13][C:12]2=[CH:14][N:15]=[CH:16][N:11]2[C:10]=1[CH3:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 196050542-Phthalimidomethyl-3-methylimidazo[5,1-b]thiazole

Product 1

HCID 196050712-Aminomethyl-3-methylimidazo[5,1-b]thiazoleYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 0.052 ml portion of anhydrous hydrazine was added to 15 ml of a dry methanol solution containing 380 mg of 2-phthalimidomethyl-3-methylimidazo[5,1-b]thiazole, followed by heating under reflux for 6 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, 15 ml of dichloromethane was added. Afterward, the solution was extracted with 15 ml of 2N hydrochloric acid, and the hydrochloric acid extract was alkalified with potassium hydroxide. The organic layer extracted from the aqueous layer with dichloromethane (40 ml×3) was dried over anhydrous potassium carbonate, followed by filtration. The solvent was then evaporated under reduced pressure to obtain 185 mg of 2-aminomethyl-3-methylimidazo[5,1-b]thiazole as a milky white powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 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, 15 ml of dichloromethane was added
  8. extractionAfterward, the solution was extracted with 15 ml of 2N hydrochloric acid
  9. extractionthe hydrochloric acid extract
  10. extractionThe organic layer extracted from the aqueous layer with dichloromethane (40 ml×3)
  11. dry with materialwas dried over anhydrous potassium carbonate
  12. filtrationfollowed by filtration
  13. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-03ed3815a89749fda8627f8b01dde2fb
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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