Hydrochloric Acid → HCID 86739959, compound

HRID 2164309Notes

Reaction equation

HRID 2164309 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](=[S:19])[C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[CH:10]=1)[NH:7][C:6](=[O:20])[CH2:5]2.Cl.[OH-:22].[Na+:23]>O>[OH2:20].[NH2:7][C:8]1[C:9]([C:11](=[S:19])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[CH2:5][C:6]([O-:20])=[O:22].[Na+:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20406153HCID 20406153, compound

Product 1

HCID 86739959HCID 86739959, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6.4 g (20.0 mmol) of 5-chloro-7-(4-methylthiobenzoyl)indolin-2-one in 110 ml of 3N sodium hydroxide was heated at 100° C. in an oil bath and stirred under a nitrogen atmosphere for 22 hrs. The reaction mixture was diluted to 600 ml with water and then titrated to a pH of 7.5 with concentrated hydrochloric acid. The mixture was then filtered and the filter cake was extracted with 1.5 liter of hot water. The filtrate obtained was concentrated to a solid residue. This residue was dissolved in hot absolute ethyl alcohol and filtered. The filtrate obtained was concentrated to a solid which was dissolved in 300 ml of 2-propanol and filtered. The filtrate obtained was concentrated to 200 ml and cooled to 0° C., whereby a gel was obtained. This gel was left at room temperature and a crystalline solid was collected therefrom by filtration and dried to give 2.9 g (39%) of the titled compound as a yellow solid, m.p. 259°-260° C.

Workup

  1. filtrationThe mixture was then filtered
  2. extractionthe filter cake was extracted with 1.5 liter of hot water
  3. customThe filtrate obtained
  4. concentrationwas concentrated to a solid residue
  5. dissolutionThis residue was dissolved in hot absolute ethyl alcohol
  6. filtrationfiltered
  7. customThe filtrate obtained
  8. concentrationwas concentrated to a solid which
  9. dissolutionwas dissolved in 300 ml of 2-propanol
  10. filtrationfiltered
  11. customThe filtrate obtained
  12. concentrationwas concentrated to 200 ml
  13. temperaturecooled to 0° C.
  14. customwhereby a gel was obtained
  15. waitThis gel was left at room temperature
  16. customa crystalline solid was collected
  17. filtrationby filtration
  18. customdried

Sources & evidence

ORD record
ord-c2267bd3b9ab4de6a01bab658e3c438b
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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