Hydrochloric Acid → HCID 178449352, compound

HRID 1462261Notes

Reaction equation

HRID 1462261 reaction equation
[CH2:1]([N:5]=[C:6]([OH:20])[C:7]1[C:8](=[C:12]([Cl:19])[C:13](Cl)=[C:14]([Cl:17])[C:15]=1[Cl:16])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>O1CCCC1>[CH2:1]([N:5]=[C:6]([OH:20])[C:7]1[C:8](=[C:12]([Cl:19])[C:13]([S:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:14]([Cl:17])[C:15]=1[Cl:16])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 178449351HCID 178449351, compound

Product 1

HCID 178449352HCID 178449352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2 g (5.86 millimols) of tetrachlorophthalic acid N-n-butylimide are initially introduced, together with 2.43 g (17.59 millimols) of potassium carbonate, into 15 ml of tetrahydrofuran at 0° C. A solution of 680 mg (6.16 millimols) of thiophenol in 10 ml of tetrahydrofuran is added dropwise over a period of 2 hours. The mixture is stirred at 0° C. for 3 hours and gradually warmed to 25° C. over a period of 6 hours, and then acidified with 2N HCl solution and extracted with tetrahydrofuran/toluene. After drying over sodium sulfate, the organic phase is evaporated and the residue is recrystallised several times. This yields 0.17 g (7% of theory) of 4-phenylthio-3,5,6-trichlorophthalic acid N-n-butylimide; melting point 159°-63° C.

Workup

  1. temperaturegradually warmed to 25° C. over a period of 6 hours
  2. extractionextracted with tetrahydrofuran/toluene
  3. dry with materialAfter drying over sodium sulfate
  4. customthe organic phase is evaporated
  5. customthe residue is recrystallised several times

Sources & evidence

ORD record
ord-96edfb1b325043d69c0d7c7249399c0d
Source dataset
uspto-grants-1984_07
Patent number
US04459414

Reaction notes

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