Phenyl chloroformate → HCID 86652638, compound

HRID 570590Notes

Reaction equation

HRID 570590 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1([C:36]2[C:37]([O:42][CH2:43][CH3:44])=[N:38][CH:39]=[CH:40][CH:41]=2)[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([Cl:21])[CH:19]=2)[N:14]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[O:33][CH3:34])(=[O:24])=[O:23])[C:13]1=[O:35]>ClCCl.N1C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])(=[O:23])=[O:24])[C:13](=[O:35])[C:12]2([NH:11][C:2](=[O:3])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:36]1[C:37]([O:42][CH2:43][CH3:44])=[N:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 67087949HCID 67087949, compound

Product 1

HCID 86652638HCID 86652638, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.83 ml (6.6 mmol) of phenyl chloroformate was slowly added dropwise to a solution, cooled to 0° C., of 2.57 g (5.1 mmol) of 3-amino-5-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-1,3-dihydroindol-2-one in 10 ml of dichloromethane and 4.1 ml of pyridine. The reaction mixture was then 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 dissolved in a little dichloromethane, and six times the volume of diisopropyl ether were added. The resulting precipitate was filtered off, washed with diisopropyl ether and dried in vacuo. 3.01 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. dissolutionThe residue was dissolved in a little dichloromethane, and six times the volume of diisopropyl ether
  6. additionwere added
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed with diisopropyl ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-20b9b7051a5b45ffbb600aea76387be3
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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