Dimethyl Sulfoxide → HCID 178426579, compound

HRID 1633425Notes

Reaction equation

HRID 1633425 reaction equation
[C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([N:7]=[C:8]([OH:27])[C:9]2[C:10](=[CH:14][C:15]([N+]([O-])=O)=[CH:16][C:17]=2C2C=CC=CC=2)[C:11]([OH:13])=S)=[CH:3][CH:2]=1.[C:29]1([S-:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Na+].C[S:38]([CH3:40])=O.[OH2:41]>>[C:1]1([CH3:28])[CH:2]=[CH:3][C:4]([N:7]=[C:8]([OH:27])[C:9]2[C:10](=[C:14]([S:38][C:40]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH:15]=[C:16]([S:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:17]=2)[C:11]([OH:13])=[O:41])=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 4110039Sodium benzenethiolateHCID 178426578HCID 178426578, compound

Product 1

HCID 178426579HCID 178426579, compound

Procedure

3.9 g (10 mmols) of 5-nitro-3-phenylthiophthalic acid N-p-toluylimide, 1.4 g (10 mmols) of sodium thiophenolate and 80 ml of dimethyl sulfoxide are stirred for one hour at 25° C. The reaction mixture is taken up in water and chloroform and the organic phase is washed with water, dried over magnesium sulfate and evaporated. After recrystallisation from toluene, 4.1 g (91% of theory) of the title imide, with a melting point of 179°-180° C., are obtained.

Workup

  1. washchloroform and the organic phase is washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customAfter recrystallisation from toluene, 4.1 g (91% of theory) of the title imide
  5. customwith a melting point of 179°-180° C., are obtained

Sources & evidence

ORD record
ord-b6a4e2485ba54342a9ca4546878cd896
Source dataset
uspto-grants-1984_10
Patent number
US04480105

Reaction notes

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