Ethyl Acetate → HCID 54070291, compound

HRID 1657608Notes

Reaction equation

HRID 1657608 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[S:17](=[O:22])(=[O:21])[N:18]([CH3:20])[CH3:19])[N:6]([CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][OH:34])[CH2:28][CH2:27]3)[C:5]=2[CH:4]=1.[C:35](Cl)(=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[S:17](=[O:21])(=[O:22])[N:18]([CH3:19])[CH3:20])[N:6]([CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH:29]([CH2:32][CH2:33][O:34][C:35](=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:30][CH2:31]3)[C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 17313Heptanoyl chlorideHCID 21534830HCID 21534830, compound

Product 1

HCID 54070291HCID 54070291, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Working in the absence of moisture, a mixture of 2-methoxy-6-dimethylsulphamoyl-10-[3-(4-hydroxyethylpiperidino)propyl]phenothiazine (11.4 g.) and heptanoyl chloride (3.8 g.) in toluene (150 cc.) is heated under reflux, with stirring, for 6 hours. After cooling, ethyl acetate (75 cc.) is added and the mixture is then rendered alkaline, without exceeding a temperature of 5°C., by adding a solution of anhydrous sodium carbonate (2.3 g.) in distilled water (75 cc.). After decanting, the aqueous layer is extracted with ethyl acetate (100 cc.). The organic extracts are combined and then washed three times with distilled water (total 240 cc.). The organic extract is dried over sodium sulphate and the solvent evaporated. 2-Methoxy-6-dimethylsulphamoyl-10-[3-(4-heptanoyloxyethylpiperidino)propyl]phenothiazine (14.4 g.), in the crude state, is thus obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customa temperature of 5°C.
  5. customAfter decanting
  6. extractionthe aqueous layer is extracted with ethyl acetate (100 cc.)
  7. washwashed three times with distilled water (total 240 cc.)
  8. extractionThe organic extract
  9. dry with materialis dried over sodium sulphate
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-925b55c362064a19ae5820f486575da4
Source dataset
uspto-grants-1976_06
Patent number
US03961055

Reaction notes

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