1-Chloroethyl chloroformate → HCID 68578547, compound

HRID 886979Notes

Reaction equation

HRID 886979 reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:22])=[C:18]([CH:19]3[CH2:21][CH2:20]3)[C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:23]C(OC(Cl)C)=O>C1(C)C=CC=CC=1>[ClH:23].[CH:19]1([C:18]2[C:12]3[O:11][CH2:10][CH2:9][NH:8][CH2:14][C:13]=3[CH:15]=[CH:16][C:17]=2[F:22])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 68580484HCID 68580484, compound

Product 1

HCID 68578547HCID 68578547, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-benzyl-9-cyclopropyl-8-fluoro-2,3,4,5-tetrahydro-1,4-benzoxazepine (408 mg, 1.37 mmol) and 1-chloroethyl chloroformate (0.178 ml, 1.65 mmol) in toluene (10 ml) was stirred at 90° C. for 2 hr, and the solvent was evaporated under reduced pressure. Methanol (10 ml) was added to the residue, the mixture was stirred at 80° C. for 1 hr, and diisopropyl ether (10 ml) was added. The precipitate was collected by filtration and recrystallized from a mixed solvent of ethanol and diisopropyl ether to give the desired product (295 mg, 88.5%) as a solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionMethanol (10 ml) was added to the residue
  3. additiondiisopropyl ether (10 ml) was added
  4. filtrationThe precipitate was collected by filtration
  5. customrecrystallized from a mixed solvent of ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-7fa7b3f06db34cdfb5336e163ab005c5
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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