HCID 15521023, compound → 2,3-Dimethylimidazo[2,1-b]thiazole-5-methanol

HRID 635838Notes

Reaction equation

HRID 635838 reaction equation
C([O:3][C:4]([C:6]1[N:13]2[C:9]([S:10][C:11]([CH3:15])=[C:12]2[CH3:14])=[N:8][CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:15][C:11]1[S:10][C:9]2=[N:8][CH:7]=[C:6]([CH2:4][OH:3])[N:13]2[C:12]=1[CH3:14]

Participants

4

Reactant 2

HCID 15521023HCID 15521023, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 155210242,3-Dimethylimidazo[2,1-b]thiazole-5-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3-Dimethylimidazo[2,1-b]thiazole-5-carboxylic acid ethyl ester (Formula A-4) (1.68 g) in THF (50 mL) at 0° was treated with LiAlH4 (0.38 g) and reacted at 25° for 1.5 hours. Excess reagent was quenched by sequential addition of water and 15% sodium hydroxide. The resulting mixture was diluted with THF (100 mL), filtered, and the filtrate was evaporated to a residue of crude 2,3-Dimethylimidazo[2,1-b]thiazole-5-methanol (Formula A-5) (1.04 g). Crystallization from isopropanol solution gave pure 2,3-Dimethylimidazo[2,1-b]thiazole-5-methanol (Formula A-5), m.p. 166-167°.

Workup

  1. customreacted at 25° for 1.5 hours
  2. customExcess reagent was quenched by sequential addition of water and 15% sodium hydroxide
  3. additionThe resulting mixture was diluted with THF (100 mL)
  4. filtrationfiltered
  5. customthe filtrate was evaporated to a residue of crude 2,3-Dimethylimidazo[2,1-b]thiazole-5-methanol (Formula A-5) (1.04 g)
  6. customCrystallization from isopropanol solution

Sources & evidence

ORD record
ord-4364517fd43d499294f13f4448b543d5
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

Loading…