Hydrochloric Acid → 5-Ethyl-6-hydroxymethyl-imidazo[2,1-b]thiazole

HRID 586378Notes

Reaction equation

HRID 586378 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[N:17]=[C:18]2[N:22]([C:23]=1[CH2:24][CH3:25])[CH:21]=[CH:20][S:19]2)=O)C.Cl.[OH-].[Na+]>C1COCC1>[CH2:24]([C:23]1[N:22]2[C:18]([S:19][CH:20]=[CH:21]2)=[N:17][C:16]=1[CH2:14][OH:13])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20825691HCID 20825691, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 223351225-Ethyl-6-hydroxymethyl-imidazo[2,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminum hydride (1M in THF, 11 mL, 11 mmol) is added to a solution of 5-ethyl-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester (800 mg, 3.6 mmol) in THF (20 mL). The mixture is stirred at room temperature for 0.5 h. HCl (10%, 2 mL) is added, and the mixture is stirred for an additional 5 min. The mixture is neutralized by the addition of sodium hydroxide (2 N) until pH is above 10 and then extracted with ethyl acetate (3×20 mL). The combined organic layers are dried and solvent removed to give 5-ethyl-6-hydroxymethyl-imidazo[2,1-b]thiazole as a solid. Step 3. Preparation of 6-chloromethyl-5-ethyl-imidazo[2,1-b]thiazole

Workup

  1. stirringthe mixture is stirred for an additional 5 min
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. customThe combined organic layers are dried
  4. customsolvent removed

Sources & evidence

ORD record
ord-256fb4f67cf74c71abe1da9f139d0d3a
Source dataset
uspto-grants-2005_08
Patent number
US06936617B2

Reaction notes

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