Hydrochloric Acid → HCID 178485482, compound

HRID 485975Notes

Reaction equation

HRID 485975 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>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C(C)=CC=CC=1.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 (6.7 millimols) of tetrachlorophthalic acid N-methylimide, 950 mg (6.9 millimols) of potassium carbonate, 120 mg (0.33 millimol) of hexadecyltrimethylammonium bromide, 20 ml of xylene and 0.86 ml of water are stirred vigorously at 100° C. and a solution of 860 mg (6.9 millimols) of p-thiocresol in 20 ml of xylene is added dropwise over a period of 10 minutes. After 30 minutes, the mixture is cooled, acidified with 2N HCl solution and extracted with methylene chloride. After drying over sodium sulfate, evaporation and recrystallisation from toluene/cyclohexane, 310 mg (12% of theory) of the title imide are obtained; melting point 209°-16° C.

Workup

  1. temperaturethe mixture is cooled
  2. extractionextracted with methylene chloride
  3. dry with materialAfter drying over sodium sulfate, evaporation and recrystallisation from toluene/cyclohexane, 310 mg (12% of theory) of the title imide
  4. customare obtained

Sources & evidence

ORD record
ord-4b63c883653a4de3b760d4f46bbd5eb5
Source dataset
uspto-grants-1985_08
Patent number
US04537977

Reaction notes

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