Acetyl chloride → HCID 15290076, compound

HRID 1460161Notes

Reaction equation

HRID 1460161 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([OH:20])[C:18]=1[OH:19])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([S:14][CH3:15])=[S:13])[CH2:8][CH2:7]1.[C:21](Cl)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:20][C:17]1[CH:16]=[C:4]([CH:3]=[C:2]([O:1][C:17](=[O:20])[CH3:16])[C:18]=1[O:19][C:2](=[O:1])[CH3:18])[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]([S:14][CH3:15])=[S:13])[CH2:10][CH2:11]1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 15290075HCID 15290075, compound

Product 1

HCID 15290076HCID 15290076, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 395 mg (1.0 mmol.) of methyl 4-(3,4,5-trihydroxybenzyl)-1-piperazinecarbodithioate was added 2 ml of dry pyridine. To the resulting suspension was added 0.22 ml (3.1 mmol.) of acetyl chloride under chilling with ice. The mixture was then stirred, and further stirred overnight at room temperature. The mixture was then extracted with ethyl acetate after addition of water. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and processed to distill off the solvent. The residue was purified by silica gel column chromatography and crystallized from ether to give 249 mg of the desired compound as a white crystalline product, m.p. 141°-143° C., yield 63.4%.

Workup

  1. temperatureunder chilling with ice
  2. customfurther stirred overnight
  3. customat room temperature
  4. extractionThe mixture was then extracted with ethyl acetate
  5. additionafter addition of water
  6. washThe extract was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationto distill off the solvent
  9. customThe residue was purified by silica gel column chromatography
  10. customcrystallized from ether

Sources & evidence

ORD record
ord-2af5de9c7fe94a838a96fc5463d01853
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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