Butanethiol → HCID 178454937, compound

HRID 1633424Notes

Reaction equation

HRID 1633424 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/2N 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-c08d039f1a824d28ae796ff963e10992
Source dataset
uspto-grants-1984_10
Patent number
US04480105

Reaction notes

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