Hydrochloric Acid → HCID 13881980, compound

HRID 543228Notes

Reaction equation

HRID 543228 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[C:6]([CH2:21][CH2:22][CH3:23])[C:5]=1[OH:24])(=[O:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].CI.Cl>C(C(C)=O)C>[CH3:25][N:18]1[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:19]=[CH:20][C:4]([C:1](=[O:3])[CH3:2])=[C:5]([OH:24])[C:6]=2[CH2:21][CH2:22][CH3:23])=[N:15][N:16]=[N:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178439680HCID 178439680, compound

Product 1

HCID 13881980HCID 13881980, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 5 g. of 5-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]-tetrazole, 3 g. of potassium carbonate, and 2.4 g. of methyl iodide in 250 ml. of methyl ethyl ketone was allowed to reflux overnight. The reaction mixture was treated with dilute hydrochloric acid and the layers were separated. The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was purified by chromatography over silica gel (2% ethanol in methylene chloride). The appropriate fractions were pooled and evaporated to an oil. Crystallization from ethyl acetate/hexane afforded 1.5 g. of the title product, m.p. about 72°-75° C.

Workup

  1. temperatureto reflux overnight
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography over silica gel (2% ethanol in methylene chloride)
  6. customevaporated to an oil
  7. customCrystallization from ethyl acetate/hexane
  8. customafforded 1.5 g

Sources & evidence

ORD record
ord-d9f95f7f81cb43fc8bc4c5e74f7bddcb
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

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