1-Chloroethyl chloroformate → HCID 68427281, compound

HRID 2191300Notes

Reaction equation

HRID 2191300 reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[ClH:26].[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][C:17]1[CH:16]=[CH:15][C:13]2[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=2[N:18]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 68429429HCID 68429429, compound

Product 1

HCID 68427281HCID 68427281, compoundYield 175.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound obtained in step 2 (0.28 g) in dichloroethane (3 mL) was added 1-chloroethyl chloroformate (0.074 mL), and the resulting mixture was stirred at 90° C. for 2 hr. The solvent was evaporated under reduced pressure, and methanol (3 mL) was added. The mixture was stirred at 80° C. for 1 hr. Diisopropyl ether (3 mL) was added, and the precipitate was collected by filtration, and recrystallized from ethanol-diisopropyl ether to give the title compound (0.21 g, 89%) as a white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure, and methanol (3 mL)
  2. additionwas added
  3. stirringThe mixture was stirred at 80° C. for 1 hr
  4. additionDiisopropyl ether (3 mL) was added
  5. filtrationthe precipitate was collected by filtration
  6. customrecrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-a656fed232984cabbad8b0f5651a4ef6
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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