Hydrochloric Acid → HCID 86742471, compound

HRID 867957Notes

Reaction equation

HRID 867957 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:17][N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)[CH2:12][CH:11]([C:13](=O)[CH3:14])[O:10][N:9]2[CH3:16])=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25].[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:17][N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)[CH2:12][CH:11]([C:13](=[N:24][OH:25])[CH3:14])[O:10][N:9]2[CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 14328896HCID 14328896, compound

Product 1

HCID 86742471HCID 86742471, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, a solution of 3.00 g (0.00938 mol) of 1-[3-(4-chlorophenyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidin-5-yl]ethanone [isomer A (3, R1 =4-Cl, R2 =CH3)], 0.69 g (0.010 mol) of hydroxylamine hydrochloride and 0.60 g (0.015 mol) of sodium hydroxide in 75 ml of ethanol is refluxed for 1 hour, cooled to ambient temperature, neutralized with 0.1N hydrochloric acid, and extracted with chloroform (2×50 ml). The combined organic extract is washed with 50 ml of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a white solid. Crystallization from ethanol gives 1.57 g (50%) of compound 4, melting point 214°-216° C. (ethanol). Anal. Calcd. for C16H19ClN4O2 : C, 57.40; H, 5.72; Cl, 10.59; N, 16.73. Found: C, 57.24; H, 5.80; Cl, 10.70; N, 16.62.

Workup

  1. extractionextracted with chloroform (2×50 ml)
  2. extractionThe combined organic extract
  3. washis washed with 50 ml of saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a white solid
  7. customCrystallization from ethanol

Sources & evidence

ORD record
ord-b2d62b76691d40a1bdd869b42bc6e485
Source dataset
uspto-grants-1988_10
Patent number
US04777264

Reaction notes

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