Hydrochloric Acid → HCID 14324517, compound

HRID 1588385Notes

Reaction equation

HRID 1588385 reaction equation
Cl[C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:3]=1.[C:33]([C:37]1[O:41][N:40]=[C:39]([OH:42])[CH:38]=1)([CH3:36])([CH3:35])[CH3:34].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[C:33]([C:37]1[O:41][N:40]([C:2]2[CH:3]=[C:4]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])[C:39](=[O:42])[CH:38]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 19755542HCID 19755542, compoundHCID 178441207HCID 178441207, compound

Product 1

HCID 14324517HCID 14324517, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 300 ml of dimethyl sulfoxide were dissolved 65 g of ethyl 4-chloro-2-hexadecyloxy-5-nitrobenzoate and 24 g of 5-t-butyl-3-hydroxyisoxazole and after adding thereto 24 g of potassium carbonate, the reaction was performed for 8 hours at 75° C. After the reaction was over, the reaction mixture obtained was poured into diluted hydrochloric acid and the product formed was extracted with ethyl acetate. After recovering and drying the organic phase thus formed, the solvent was distilled off from the organic phase and the residue thus formed was carefully applied to silica gel column chromatography, whereby the aforesaid compound was obtained as the main product. The product thus obtained was recrystallized from a mixture of methanol and acetonitrile to provide 30.1 g of the desired compound with a yield of 37.9%. The melting point thereof was 35° C. to 36° C.

Workup

  1. additionafter adding
  2. customobtained
  3. customthe product formed
  4. extractionwas extracted with ethyl acetate
  5. customAfter recovering
  6. customdrying the organic phase
  7. customthus formed
  8. distillationthe solvent was distilled off from the organic phase
  9. customthe residue thus formed
  10. customwas obtained as the main product
  11. customThe product thus obtained
  12. customwas recrystallized from a mixture of methanol and acetonitrile

Sources & evidence

ORD record
ord-451b210108e14b36a54e03c6f6e0469a
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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