Hydrochloric Acid → HCID 6483421, compound

HRID 1681914Notes

Reaction equation

HRID 1681914 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)[CH:5]=[C:6]([CH3:20])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:14](=O)[C:15]([F:18])([F:17])[F:16].Cl.[NH2:28][OH:29].Cl.O>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)[CH:5]=[C:6]([CH3:20])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]1[O:29][N:28]=[C:14]([C:15]([F:18])([F:17])[F:16])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 443297Hydroxyamine hydrochloride2×HCID 9998962HCID 9998962, compound

Product 1

HCID 6483421HCID 6483421, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 479 mg of 3-{3,5-dimethyl-4-[3-(trifluoroacetylethinyl)propoxy]phenyl}-5-methyl-1,2,4-oxadiazole from part (a) above and 509 mg hydroxylamine hydrochloride in 10 mls of acetic acid at ambient room temperature was added with stirring 1 ml 1M hydrochloric acid. After twenty hours an additional 1 ml 1M aqueous hydrochloric acid and 1.00 g hydroxylamine hydrochloride were added and stirring was continued for five days. The reaction mixture was poured into 200 mls water and extracted with ethyl ether. The ethyl ether extracts were washed with water, dried (Na2SO4) and concentrated. A solution of the residue (470 mg) in benzene was heated at reflux overnight, cooled, diluted with methylene chloride, washed with aqueous 1.5M potassium bicarbonate and water, filtered through silica gel and concentrated. The oily residue was subjected to preparative TLC (silica gel; methylene dichloride) to yield 92 mg of the title compound, m.p. 62°-64.5° C.

Workup

  1. extractionextracted with ethyl ether
  2. washThe ethyl ether extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. temperatureA solution of the residue (470 mg) in benzene was heated
  6. temperatureat reflux overnight
  7. temperaturecooled
  8. additiondiluted with methylene chloride
  9. washwashed with aqueous 1.5M potassium bicarbonate and water
  10. filtrationfiltered through silica gel
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a2ae63b6cdbf48208613d1674c74b1ea
Source dataset
uspto-grants-1992_12
Patent number
US05175177

Reaction notes

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