Acetic Anhydride → HCID 54339084, compound

HRID 1902572Notes

Reaction equation

HRID 1902572 reaction equation
CN=[C:3]([OH:19])[C:4]1[C:5](=[C:9]([N+]([O-])=O)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:28]=[C:29]([SH:34])[CH:30]=[CH:31][C:32]=1[Cl:33].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([S:34][C:9]2[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=[C:4]3[C:3]([O:7][C:6](=[O:8])[C:5]=23)=[O:19])[CH:30]=[CH:31][C:32]=1[Cl:33]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 799643,4-DichlorobenzenethiolHCID 178485491HCID 178485491, compound

Product 1

HCID 54339084HCID 54339084, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

18.84 g (75 mmols) of 3,5-dinitrophthalic acid N-methylimide [prepared according to Example 2] are initially introduced into 250 ml of ethyl acetate and treated with 30.4 g (220 mmols) of ground, anhydrous potassium carbonate, and 14 g (78 mmols) of 3,4-dichlorothiophenol are then added dropwise. After the addition of 95 ml of tetrahydrofuran, the mixture is stirred overnight and then evaporated to dryness. The residue is kept under reflux overnight in 100 ml of water, the mixture is extracted at 25° C. with petroleum ether and filtered and the aqueous filtrate is acidified with 300 ml of 2 N HCl and heated under reflux. After 2.5 hours, the mixture is cooled and extracted with tetrahydrofuran/toluene and the extract is washed with saturated NaCl solution, dried over sodium sulfate and evaporated. The residue is warmed to the reflux temperature with 100 ml of toluene and 7.66 g (75 mmols) of acetic anhydride and, after cooling, the mixture is evaporated. After recrystallisation from methylene chloride/n-pentane, 22.2 g (80% of theory) of 3-(3,4-dichlorophenylthio)-5-nitrophthalic anhydride are obtained; melting point: 154°-7° C.

Workup

  1. additionare then added dropwise
  2. customevaporated to dryness
  3. temperatureunder reflux overnight in 100 ml of water
  4. extractionthe mixture is extracted at 25° C. with petroleum ether
  5. filtrationfiltered
  6. temperatureheated
  7. temperatureunder reflux
  8. waitAfter 2.5 hours
  9. temperaturethe mixture is cooled
  10. extractionextracted with tetrahydrofuran/toluene
  11. washthe extract is washed with saturated NaCl solution
  12. dry with materialdried over sodium sulfate
  13. customevaporated
  14. temperatureafter cooling
  15. customthe mixture is evaporated
  16. customAfter recrystallisation from methylene chloride/n-pentane, 22.2 g (80% of theory) of 3-(3,4-dichlorophenylthio)-5-nitrophthalic anhydride
  17. customare obtained

Sources & evidence

ORD record
ord-6586c77be1f5418d9255e98da71e4c8d
Source dataset
uspto-grants-1982_12
Patent number
US04363917

Reaction notes

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