Triethylamine → 7-Benzoyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one

HRID 1283624Notes

Reaction equation

HRID 1283624 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:16][S:17][CH2:18][C:19](OCC)=[O:20].C(OCl)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:2]=1[NH:1][C:19](=[O:20])[CH:18]2[S:17][CH3:16])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 760802-AminobenzophenoneHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 129235507-Benzoyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-65 °C

Procedure

A solution of 300 g. (1.52 mole) of 2-aminobenzophenone in 4 liters of methylene chloride was chilled to -40°C. and then treated with 204 g. (1.52 mole) of the ethyl α-(methylthio)acetate dissolved in 5 liters of methylene chloride. The reaction mixture was then cooled to -65°C. and treated dropwise with 500 ml. of a methylene chloride solution containing 164 g. (1.52 mole) of t-butylhypochlorite. After addition was complete, stirring was continued for 2 hr. at -70°C. The solution was then treated with 182 g. (1.8 mole) of triethylamine and allowed to come to room temperature overnight. The methylene chloride solution was washed twice with 3 liters of ice water followed by drying over sodium sulfate and concentrating the dried solution to a yellow oil under reduced pressure. The oil was taken into 1.5 liters of methanol treated with 1 liter of lN hydrochloric acid and refluxed for 2 hrs. After cooling in an ice bath 343 g. (79.9%) of crude product was recovered after filtering and drying. Two recrystallizations from toluene gave creamy white flakes; m.p. 130°C.

Workup

  1. additiontreated with 204 g
  2. additiontreated dropwise with 500 ml
  3. additionAfter addition
  4. customat -70°C
  5. additionThe solution was then treated with 182 g
  6. waitto come to room temperature overnight
  7. washThe methylene chloride solution was washed twice with 3 liters of ice water
  8. dry with materialby drying over sodium sulfate
  9. concentrationconcentrating the dried solution to a yellow oil under reduced pressure
  10. additiontreated with 1 liter of lN hydrochloric acid
  11. temperaturerefluxed for 2 hrs
  12. temperatureAfter cooling in an ice bath 343 g
  13. custom(79.9%) of crude product was recovered
  14. filtrationafter filtering
  15. customdrying
  16. customTwo recrystallizations from toluene
  17. customgave creamy white flakes

Sources & evidence

ORD record
ord-cf04c68d0cac477890b091db30907067
Source dataset
uspto-grants-1976_08
Patent number
US03975531

Reaction notes

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