Benzoyl chloride → HCID 12851451, compound

HRID 355097Notes

Reaction equation

HRID 355097 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:27]Cl>O.C(Cl)(Cl)Cl>[Cl:27][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2][CH2:3]2

Participants

8

Reactant 5

HCID 7412Benzoyl chlorideHCID 10328IndolineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24526Chlorine

Product 1

HCID 12851451HCID 12851451, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6212ChloroformSolvent

Procedure

A mixture of 714 g (6 moles) of indoline and 1500 ml of chloroform and 528 g (6.6 moles) of aqueous sodium hydroxide solution (50%) was stirred at 20° to 30° C. while adding 928 g (6.6 moles) of benzoyl chloride thereto and the mixture was stirred for one hour after which 300 ml of water and 351 g (3.3 moles) of sodium carbonate were added thereto. 468.5 g (6.6 moles) of chlorine were added to the mixture with vigorous stirring and water cooling over 51/2 hours to keep the temperature below 30° C. The mixture was stirred for 30 minutes and after the addition of 1500 ml of water, the mixture was stirred for 15 minutes. The decanted organic phase was evaporated to dryness under reduced pressure at 130° C. and the residue was taken up in 1200 ml of isopropanol. The mixture was heated with stirring until complete dissolution occured and the mixture was cooled and stirred at 20°-25° C. for one hour. The mixture was vacuum filtered to obtain 5-chloro-1-benzoyl-indoline melting at 135°- 136° C.

Workup

  1. additionwere added
  2. stirringwith vigorous stirring
  3. custom2 hours
  4. customthe temperature below 30° C
  5. stirringThe mixture was stirred for 30 minutes
  6. stirringthe mixture was stirred for 15 minutes
  7. customThe decanted organic phase was evaporated to dryness under reduced pressure at 130° C.
  8. temperatureThe mixture was heated
  9. stirringwith stirring until complete dissolution
  10. temperaturethe mixture was cooled
  11. stirringstirred at 20°-25° C. for one hour
  12. filtrationfiltered

Sources & evidence

ORD record
ord-704ab6ec819145f683100ac309263538
Source dataset
uspto-grants-1983_03
Patent number
US04377699

Reaction notes

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