Water → 5-Acetoxymethylimidazo[5,1-b]thiazole

HRID 1376618Notes

Reaction equation

HRID 1376618 reaction equation
[OH:1][CH2:2][C:3]1[N:10]2[C:6]([S:7][CH:8]=[CH:9]2)=[CH:5][N:4]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].O>ClCCl>[C:11]([O:1][CH2:2][C:3]1[N:10]2[C:6]([S:7][CH:8]=[CH:9]2)=[CH:5][N:4]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 183599875-Hydroxymethylimidazo[5,1-b]thiazole

Product 1

HCID 229166655-Acetoxymethylimidazo[5,1-b]thiazoleYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.231 g (1.50 mmol) of the 5-Hydroxymethylimidazo[5,1-b]thiazole prepared in Preparation 10 in 8 ml of dichloromethane was added 0.156 ml (1.65 mmol) of acetic anhydride with ice-cooling, and the mixture was stirred at room temperature for 20 hours. To the reaction solution were added water and a saturated aqueous solution of sodium hydrogencarbonate, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography using silica gel, eluting with a 30:1 mixture of chloroform and methanol to give 0.237 g (yield 81%) of the title compound.

Workup

  1. temperaturecooling
  2. extractiona saturated aqueous solution of sodium hydrogencarbonate, and the mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by flash column chromatography
  6. washeluting with a 30:1 mixture of chloroform and methanol

Sources & evidence

ORD record
ord-3c2750eb28de434c97b5a8906f065299
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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