Hydrochloric Acid → 2,2-dimethyl-3-oxo-N-(2,4,6-trimethoxyphenyl)-tetradecanamide

HRID 1198046

반응식

HRID 1198046 반응식
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[C:8]=1[NH2:9].C([O:20][C:21](=O)[C:22]([CH3:37])([CH3:36])[C:23](=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])C.Cl>C1C=CC=CC=1>[CH3:37][C:22]([CH3:36])([C:23](=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:21]([NH:9][C:8]1[C:10]([O:16][CH3:17])=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:7]=1[O:6][CH3:5])=[O:20]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 842712,4,6-TrimethoxyanilineHCID 100632932,2-Dimethyl-3-oxo-tetradecanoic acid ethyl esterHCID 16682925Trimethylaluminum

생성물 1

HCID 100486152,2-dimethyl-3-oxo-N-(2,4,6-trimethoxyphenyl)-tetradecanamide수율 26%

시약·촉매·용매 1

HCID 241Benzene용매3회

반응 조건

온도
5 °C

실험 절차

To a flask containing 10 mL benzene which had been flushed with nitrogen, trimethylaluminum (2.0M hexane solution, 0.003 mol, 1.14 eq) was added dropwise and cooled to 5° C. A solution of 2,4,6-trimethoxyaniline (0.653 g, 0.003 mol) in 1.5 mL benzene was added dropwise (exotherm to 10° C.) and stirred for 20 minutes at 5° C. The ice bath was removed and the contents were allowed to gradually warm to room temperature over a 45-minute period. A solution of 2,2-dimethyl-3-oxo-tetradecanoic acid ethyl ester (1.0 g, 0.003 mol) in 1.5 mL benzene was added dropwise and the resulting reaction mixture was heated to reflux for 16 hours (M. F. Lipton, et al, Org. Syn. Coll. Vol. 2, 492). After cooling to room temperature, the mixture was hydrolyzed slowly with 2% HCl solution (5 mi) and stirred for 20 minutes. The layers were then separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo (30° C.) to yield a residue which was washed with hot hexanes, cooled, filtered, and oven-dried to yield 0.340 g (0.78 mmol, 26%) of the title compound, mp 92°-94° C.

후처리

  1. additionwas added dropwise
  2. customThe ice bath was removed
  3. temperatureto gradually warm to room temperature over a 45-minute period
  4. customthe resulting reaction mixture
  5. temperaturewas heated
  6. temperatureto reflux for 16 hours (M. F. Lipton, et al, Org. Syn. Coll. Vol. 2, 492)
  7. temperatureAfter cooling to room temperature
  8. stirringstirred for 20 minutes
  9. customThe layers were then separated
  10. extractionthe aqueous layer was extracted three times with ethyl acetate
  11. washThe combined organic layers were washed with brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated in vacuo (30° C.)
  14. customto yield a residue which
  15. washwas washed with hot hexanes
  16. temperaturecooled
  17. filtrationfiltered
  18. customoven-dried

출처 및 근거

ORD 기록
ord-64fb43b553ec4509999e44df3ba2e163
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278326

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