Ethyl Acetate → HCID 178485492, compound

HRID 1633422Notes

Reaction equation

HRID 1633422 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].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+].[Cl:32][C:33]1[CH:34]=[C:35]([SH:40])[CH:36]=[CH:37][C:38]=1[Cl:39]>O1CCCC1>[CH3:1][N:2]=[C:3]([OH:19])[C:4]1[C:5](=[C:9]([S:40][C:35]2[CH:36]=[CH:37][C:38]([Cl:39])=[C:33]([Cl:32])[CH:34]=2)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 799643,4-DichlorobenzenethiolHCID 178485491HCID 178485491, compound

Product 1

HCID 178485492HCID 178485492, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.09 g (80 mmols) of 3,5-dinitrophthalic acid N-methylimide [prepared according to Example 2] are initially introduced into 300 ml of ethyl acetate and treated with 33.6 g (243 mmols) of ground, anhydrous potassium carbonate, and 15.04 g (84 mmols) of 3,4-dichlorothiophenol are then added dropwise at 25° C. After the addition of 100 ml of tetrahydrofuran, the mixture is stirred overnight and evaporated to dryness and the residue is taken up in a mixture of methylene chloride and dilute hydrochloric acid. The organic phase is washed with saturated NaCl solution, dried over sodium sulfate and evaporated. After recrystallisation from methylene chloride/n-pentane, 25.74 g (84% of theory) of the title imide, with a melting point of 167°-8° C., are obtained.

Workup

  1. additionare then added dropwise at 25° C
  2. customevaporated to dryness
  3. additionthe residue is taken up in a mixture of methylene chloride and dilute hydrochloric acid
  4. washThe organic phase is washed with saturated NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customAfter recrystallisation from methylene chloride/n-pentane, 25.74 g (84% of theory) of the title imide
  8. customwith a melting point of 167°-8° C., are obtained

Sources & evidence

ORD record
ord-8a94a370355d4d39b82dadb2ca7a5edb
Source dataset
uspto-grants-1984_10
Patent number
US04480105

Reaction notes

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