Allyl chloroformate → HCID 19605026, compound

HRID 1603476Notes

Reaction equation

HRID 1603476 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[N:5]2[CH:11]=[N:10][CH:9]=[C:6]2[S:7][CH:8]=1.OCC1N2C=NC=C2SC=1.Cl[C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24].C(=O)([O-])O.[Na+]>O.ClCCl>[CH2:26]([O:25][C:23]([N:2]([CH2:3][C:4]1[N:5]2[CH:11]=[N:10][CH:9]=[C:6]2[S:7][CH:8]=1)[CH3:1])=[O:24])[CH:27]=[CH2:28]

Participants

7

Reactant 4

HCID 18052Allyl chloroformateHCID 516892Sodium BicarbonateHCID 15428311HCID 15428311, compoundHCID 19605154HCID 19605154, compound

Product 1

HCID 19605026HCID 19605026, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 207 mg of a mixture of 3-(N-methylamino)methylimidazo[5,1-b]thiazole and 3-hydroxymethylimidazo[5,1-b]thiazole in a ratio of about 1:1, 10 ml of dichloromethane and 3 ml of water were added, and then 0.092 ml of allyl chloroformate was added thereto under ice-cooling. The mixture was stirred for 30 minutes under ice-cooling, while the aqueous layer was adjusted to pH 8.5 by adding a sodium hydrogencarbonate solution. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 73.6 mg of the title compound.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling, while the aqueous layer
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-cceee729e7dc43f9b5b1be37e531002f
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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