Sodium hydride → HCID 12899552, compound

HRID 621566Notes

Reaction equation

HRID 621566 reaction equation
[OH:1][CH:2]([CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2.[H-].[Na+].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([O:44][CH3:45])[C:41]=1[O:42][CH3:43])[C:36](Cl)=[O:37]>C1(C)C(C)=CC=CC=1>[CH3:45][O:44][C:40]1[CH:39]=[C:35]([CH:34]=[C:33]([O:32][CH3:31])[C:41]=1[O:42][CH3:43])[C:36]([O:1][CH:2]([CH2:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:22]1)[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2)=[O:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 12899426HCID 12899426, compound

Product 1

HCID 12899552HCID 12899552, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.9 grams of 5-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril and 0.24 g of sodium hydride are dispersed in 40 ml of xylene and heated for 1 hour under refluxing conditions. Then the bath temperature is lowered to 130° C. and 1.40 g of 3,4,5-trimethoxybenzoyl chloride are added gradually and heated for 8 hours under refluxing condition. Xylene is removed from the reaction mixture by distillation, then the residue is poured into 80 ml of water and extracted with chloroform. The chloroform layer is washed with water, dried and chloroform is removed by distillation. The residue is recrystallized from ethanol to obtain 1.5 g of 5-[2-(3,4,5-trimethoxybenzoyloxyl)-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless crystals with a melting point of 125°-127° C.

Workup

  1. temperatureheated for 1 hour under refluxing conditions
  2. customis lowered to 130° C.
  3. temperatureheated for 8 hours
  4. temperatureunder refluxing condition
  5. customXylene is removed from the reaction mixture by distillation
  6. additionthe residue is poured into 80 ml of water
  7. extractionextracted with chloroform
  8. washThe chloroform layer is washed with water
  9. customdried
  10. customchloroform is removed by distillation
  11. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-4921aa4e3a82430e8939b4b64aec3b35
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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