Hydrochloric Acid → HCID 54071604, compound

HRID 1633428Notes

Reaction equation

HRID 1633428 reaction equation
CN=[C:3]([OH:21])[C:4]1[C:5](=[C:9]([S:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7].Cl>[OH-].[Na+]>[CH2:17]([S:16][C:9]1[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=[C:4]2[C:3]([O:7][C:6](=[O:8])[C:5]=12)=[O:21])[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454937HCID 178454937, compound

Product 1

HCID 54071604HCID 54071604, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

883 mg (3 mmols) of 3-n-butylthio-5-nitrophthalic acid N-methylimide are kept under reflux overnight in 9 ml of 1N sodium hydroxide solution and the mixture is acidified with 10 ml of 2N hydrochloric acid and, after 5 minutes under reflux, cooled. The mixture is extracted with tetrahydrofuran/toluene and the extracts are washed with saturated NaCl solution, dried over sodium sulfate and evaporated. The resulting acid is converted to the anhydride with 1 ml of acetic anhydride and 10 ml of toluene, by heating and evaporation. After recrystallisation from cyclohexane, 790 mg (94% of theory) of the title anhydride are obtained as a yellow product; melting point: 95°-97° C.

Workup

  1. temperatureunder reflux
  2. temperaturecooled
  3. extractionThe mixture is extracted with tetrahydrofuran/toluene
  4. washthe extracts are washed with saturated NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. temperatureby heating
  8. customevaporation
  9. customAfter recrystallisation from cyclohexane, 790 mg (94% of theory) of the title anhydride
  10. customare obtained as a yellow product

Sources & evidence

ORD record
ord-0f6f2a7ae1a24cf0a26130ba07759e01
Source dataset
uspto-grants-1984_10
Patent number
US04480105

Reaction notes

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