Hydroxyamine hydrochloride → HCID 76543197, 화합물

HRID 2214874노트

반응식

HRID 2214874 반응식
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([CH:29]=O)[C:13]2[O:18][CH:17]([C:19]([F:22])([F:21])[F:20])[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][C:14]=2[CH:28]=1>C(O)C.O>[Cl:9][C:10]1[CH:11]=[C:12]([CH:29]=[N:2][OH:3])[C:13]2[O:18][CH:17]([C:19]([F:22])([F:21])[F:20])[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][C:14]=2[CH:28]=1

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 21883599HCID 21883599, 화합물

생성물 1

HCID 76543197HCID 76543197, 화합물

시약·촉매·용매 1

HCID 19096565Water ethanol용매2회

실험 절차

Hydroxylamine hydrochloride (1.30 g, 18.7 mmol), sodium acetate (1.50 g, 19.4 mmol), and a mixture of ethanol-water (80:20, 15 mL) were stirred at room temperature for 0.4 hours. The aldehyde (Example 76, Step 3)(3.07 g, 9.0 mmol) was dissolved in a solution of ethanol-water (4:1, 25 mL) and added to this mixture and stirred at 100° C. for 1 hour. The reaction was filtered hot and the filtrate allowed to cool to room temperature. An orange solid crystallized in the filtrate which was collected by vacuum filtration. The solid was dissolved in ethyl acetate and the solution washed with water, brine, dried over MgSO4, concentrated in vacuo. The resulting solid was recrystallized from ethyl acetate-hexane yielding the oxime as a tan powder (1.50 g, 47%): mp 186.6–187.6° C. 1H NMR (acetone-d6/300 MHz) 10.87 (s, 1H), 8.34 (s, 1H), 7.90 (s, 1H), 7.77 (d, 1H, J=2.6 Hz), 7.60 (d, 1H, J=2.6 Hz), 6.02 (q, 1H, J=7.1 Hz), 4.35 (m, 2H), 1.34 (t, 3H, J=7.0 Hz).

후처리

  1. additionadded to this mixture
  2. stirringstirred at 100° C. for 1 hour
  3. filtrationThe reaction was filtered hot
  4. temperatureto cool to room temperature
  5. customAn orange solid crystallized in the filtrate which
  6. filtrationwas collected by vacuum filtration
  7. dissolutionThe solid was dissolved in ethyl acetate
  8. washthe solution washed with water, brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid was recrystallized from ethyl acetate-hexane yielding the oxime as a tan powder (1.50 g, 47%)

출처 및 근거

ORD 기록
ord-99a90587013046d287dca41d3fbf6a8b
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109211B2

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