Hydrochloric Acid → HCID 178485482, compound

HRID 485976Notes

Reaction equation

HRID 485976 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-a4debe35dc694d7fbe04d4cbe760aea6
Source dataset
uspto-grants-1985_08
Patent number
US04537977

Reaction notes

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