Phenyl chloroformate → HCID 67088001, compound

HRID 570591Notes

Reaction equation

HRID 570591 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([C:23]1[C:24]([O:29][CH2:30][CH3:31])=[N:25][CH:26]=[CH:27][CH:28]=1)[OH:22]>N1C=CC=CC=1.ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3])[C:16](=[O:21])[C:15]2([C:23]1[C:24]([O:29][CH2:30][CH3:31])=[N:25][CH:26]=[CH:27][CH:28]=1)[O:22][C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3]

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 67088040HCID 67088040, compound

Product 1

HCID 67088001HCID 67088001, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

2.6 ml (21 mmol) of phenyl chloroformate were slowly added dropwise to a solution, cooled to 0° C., of 3.00 g (9.8 mmol) of 5-chloro-3-(2-ethoxypyridin-3-yl)-3-hydroxy-1,3-dihydroindol-2-one from example a.1 in 10 ml of pyridine, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and extracted with water. The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was stirred with diethyl ether. 2.58 g of the title compound were obtained as a white solid.

Workup

  1. extractionextracted with water
  2. washThe organic phase was washed with water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. stirringThe residue was stirred with diethyl ether

Sources & evidence

ORD record
ord-335fdbb927664a0db07e69453a70a000
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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