Hydrochloric Acid → HCID 178485482, compound

HRID 1462277Notes

Reaction equation

HRID 1462277 reaction equation
[CH3:1][N:2]=[C:3]([OH:17])[C:4]1[C:5](=[C:9]([Cl:16])[C:10](Cl)=[C:11]([Cl:14])[C:12]=1[Cl:13])[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=1.Cl>C1(C)C(C)=CC=CC=1.[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.O>[CH3:1][N:2]=[C:3]([OH:17])[C:4]1[C:5](=[C:9]([Cl:16])[C:10]([S:31][C:28]2[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=2)=[C:11]([Cl:14])[C:12]=1[Cl:13])[C:6]([OH:8])=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78114-MethylbenzenethiolHCID 11430Potassium CarbonateHCID 178485481HCID 178485481, compound

Product 1

HCID 178485482HCID 178485482, compound

Reagents, catalysts & solvents 3

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent2×

Procedure

2 g (6.69 millimols) of tetrachlorophthalic acid N-methylimide are dissolved in 20 ml of xylene at 100° C.; 0.86 ml of water, 0.95 g of potassium carbonate and 120 mg of hexadecyltrimethylammonium bromide are added and a solution of 0.86 g (6.89 millimols) of p-thiocresol in 1 ml of xylene is added dropwise at 100° C. After 30 minutes, the mixture is cooled, acidified with 2N HCl solution and extracted with methylene chloride. The solution is dried with sodium sulfate and evaporated and the residue is recrystallised from toluene/cyclohexane. This yields 0.69 g (27%) of the title compound; melting point 212°-216°.

Workup

  1. temperaturethe mixture is cooled
  2. extractionextracted with methylene chloride
  3. dry with materialThe solution is dried with sodium sulfate
  4. customevaporated
  5. customthe residue is recrystallised from toluene/cyclohexane

Sources & evidence

ORD record
ord-9bc1c631420d42ea8541f2aa24f125db
Source dataset
uspto-grants-1984_07
Patent number
US04459414

Reaction notes

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