1-Chloroethyl chloroformate → HCID 68427383, compound

HRID 2191303Notes

Reaction equation

HRID 2191303 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]=[C:22]([Cl:26])[CH:21]=3)=[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:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=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 68428722HCID 68428722, compound

Product 1

HCID 68427383HCID 68427383, compoundYield 183.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound obtained in step 2 (0.23 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 (0.18 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-10bb29d7d1a147a2a4c7fefd38d45f5a
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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