1-Chloroethyl chloroformate → HCID 68579320, compound

HRID 886981Notes

Reaction equation

HRID 886981 reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:24])=[C:18]([C:19]3[CH:23]=[CH:22][O:21][CH:20]=3)[C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:25]C(OC(Cl)C)=O>C1(C)C=CC=CC=1>[ClH:25].[F:24][C:17]1[CH:16]=[CH:15][C:13]2[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=2[C:18]=1[C:19]1[CH:23]=[CH:22][O:21][CH:20]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 68578117HCID 68578117, compound

Product 1

HCID 68579320HCID 68579320, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-benzyl-8-fluoro-9-furan-3-yl-2,3,4,5-tetrahydro-1,4-benzoxazepine (104 mg, 0.323 mmol), 1-chloroethyl chloroformate (0.0418 ml, 0.387 mmol) in toluene (2 ml) was stirred at 90° C. for 2 hr, and the solvent was evaporated under reduced pressure. Water and 1N sodium hydroxide were added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1). To ethyl acetate solution of the residue was added 4N hydrogen chloride-ethyl acetate. The precipitate was collected by filtration and was recrystallized from a mixed solvent of ethanol and diisopropyl ether to give the desired product (28 mg, 32.3%) as a solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater and 1N sodium hydroxide were added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1)
  8. additionTo ethyl acetate solution of the residue was added 4N hydrogen chloride-ethyl acetate
  9. filtrationThe precipitate was collected by filtration
  10. customwas recrystallized from a mixed solvent of ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-2cdca37699454a06b2de2aa6b430025f
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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