Hydrochloric Acid → 5-ethoxycarbonyl-4-(2-ethoxy-6-pentadecylphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

HRID 2246409노트

반응식

HRID 2246409 반응식
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([CH3:8])=O)[CH3:2].[CH2:10]([O:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:14]=1[CH:15]=O)[CH3:11].[NH2:36][C:37]([NH2:39])=[O:38].Cl>O1CCCC1>[CH2:1]([O:3][C:4]([C:5]1[CH:15]([C:14]2[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:18][CH:19]=[CH:20][C:13]=2[O:12][CH2:10][CH3:11])[NH:36][C:37](=[O:38])[NH:39][C:6]=1[CH3:8])=[O:9])[CH3:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 8868Ethyl AcetoacetateHCID 225745702-Ethoxy-6-pentadecyl benzaldehyde

생성물 1

HCID 104365325-ethoxycarbonyl-4-(2-ethoxy-6-pentadecylphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethylacetoacetate (1.25 g, 8.5 mmol), 2-ethoxy-6-pentadecyl benzaldehyde (3 g, 8.5 mmol) and urea (1.1 g, 17 mmol) in tetrahydrofuran (20 mL) was heated to reflux (65-70° C.) in the presence of hydrochloric acid (30%) for 7 h. The reaction mixture after being cooled to room temperature was poured into crushed ice (20 g) and stirred for 5 min. The viscous liquid was extracted with ethylacetate (40 mL) and was washed with 1N hydrochloric acid, water, sodium bicarbonate and brine. After drying over anhydrous sodium sulfate, the solvent was evaporated to yield light yellow oil. This crude product was purified by flash column chromatography and recrystallized from hexane to get white crystalline solid of title compound.

후처리

  1. additionwas poured
  2. extractionThe viscous liquid was extracted with ethylacetate (40 mL)
  3. washwas washed with 1N hydrochloric acid, water, sodium bicarbonate and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customto yield light yellow oil
  7. customThis crude product was purified by flash column chromatography
  8. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-803326eccd53404486e9491a5f789b43
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687511B2

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