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

HRID 596906Notes

Reaction equation

HRID 596906 reaction equation
[CH3:1][S:2]([CH2:4][C:5]([C:7]1[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=1[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6])=O.C1C=CC=CC=1.FC(F)(F)C(O)=O>>[C:10]([N:9]1[C:8]2[C:7](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5](=[O:6])[CH:4]1[S:2][CH3:1])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 6422Trifluoroacetic acidHCID 21414519N-{2-[(Methanesulfinyl)acetyl]phenyl}benzamide

Product 1

HCID 214145221-Benzoyl-2-(methylsulfanyl)-1,2-dihydro-3H-indol-3-oneYield 68.4%

Procedure

2'-[(methylsulfinyl)-acetyl]benzanilide (7 g) is refluxed in benzene containing 1 equivalent of trifluoroacetic acid for 1 hour. The solvents are removed under reduced pressure to give an oil which crystallizes on standing. Recrystallization from ethyl acetate gives 1-benzoyl-2-(methylthio)-3-indolinone (4.5 g 67%) m.p. 126°-128° C.

Workup

  1. customThe solvents are removed under reduced pressure
  2. customto give an oil which
  3. customcrystallizes
  4. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-1e471593b6b94fbea263196c39aad99c
Source dataset
uspto-grants-1977_03
Patent number
US04012422

Reaction notes

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