Hydrochloric Acid → 2-(Methylsulfinyl)-2'-(4-methoxyanilino)acetophenone

HRID 1439207Notes

Reaction equation

HRID 1439207 reaction equation
[Na+].[CH3:2][S:3]([CH2-:5])=[O:4].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2C(=O)O[C:17](=[O:18])[C:16]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:15]23)=[CH:10][CH:9]=1.Cl.C(Cl)Cl>CS(C)=O>[CH3:2][S:3]([CH2:5][C:17]([C:16]1[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=1[NH:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1)=[O:18])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10154010Methane, sulfinylbis-, ion(1-), sodiumHCID 13505629N-(4-methoxyphenyl)isatoic anhydride

Product 1

HCID 213985852-(Methylsulfinyl)-2'-(4-methoxyanilino)acetophenone

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a 2 molar solution of dimsyl sodium in dimethylsulfoxide (365 ml.), cooled to 10° C., was added a solution of 65 g. of N-(4-methoxyphenyl)isatoic anhydride in 150 ml. dimethylsulfoxide with stirring and stirring was continued 30 minutes at room temperature and 1 hour at 50° C. The reaction mixture was poured onto 1200 g. of ice, 70 ml. of concentrated hydrochloric acid was added, and the mixture was extrated with methylene dichloride. The extract was washed with water, dried (MgSO4), and concentrated under reduced pressure to give, after recrystallization from benzenecyclohexane 45 g. 2-(methylsulfinyl)-2'-(4-methoxyanilino)acetophenone; m.p. 115°-116° C.

Workup

  1. additionwas added a solution of 65 g
  2. additionThe reaction mixture was poured onto 1200 g
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give
  7. customafter recrystallization from benzenecyclohexane 45 g

Sources & evidence

ORD record
ord-18cc19e3c4ae4d3c9294d7edab819cf8
Source dataset
uspto-grants-1977_11
Patent number
US04058532

Reaction notes

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