Butanethiol → HCID 178454937, compound

HRID 1902567Notes

Reaction equation

HRID 1902567 reaction equation
[CH3:1][N:2]=[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].[CH2:20]([SH:24])[CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:1][N:2]=[C:3]([OH:19])[C:4]1[C:5](=[C:9]([S:24][CH2:20][CH2:21][CH2:22][CH3:23])[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 8012ButanethiolHCID 11430Potassium CarbonateHCID 178485491HCID 178485491, compound

Product 1

HCID 178454937HCID 178454937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25.1 g (100 mmols) of 3,5-dinitrophthalic acid N-methylimide, 19.8 g (220 mmols) of n-butylmercaptan, 41.5 g (300 mmols) of anhydrous potassium carbonate and 250 ml of absolute tetrahydrofuran are kept under reflux overnight. The reaction mixture is filtered, the filtrate is evaporated and the residue is taken up in methylene chloride/2 N HCl. The extracts are washed with saturated NaCl solution, dried over sodium sulfate and evaporated. After recrystallisation from cyclohexane, 11.96 g (41% of theory) of the title imide are obtained; melting point: 106°-108° C.

Workup

  1. temperatureunder reflux overnight
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. washThe extracts are washed with saturated NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customAfter recrystallisation from cyclohexane, 11.96 g (41% of theory) of the title imide
  8. customare obtained

Sources & evidence

ORD record
ord-fb633e4c022648788c92e0d16693df6e
Source dataset
uspto-grants-1982_12
Patent number
US04363917

Reaction notes

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