Hydrochloric Acid → 4-(3-methyl-4-nitrophenyl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one

HRID 422046

반응식

HRID 422046 반응식
[NH:1]=[C:2]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=1)/[CH:3]=[C:4](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH3:15])\[NH2:5].N[C:27](N)=[O:28].Cl>C(O)C.O1CCOCC1>[CH3:25][C:18]1[CH:17]=[C:16]([C:2]2[CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[O:12][CH2:13][CH2:14][CH3:15])[NH:5][C:27](=[O:28])[N:1]=2)[CH:21]=[CH:20][C:19]=1[N+:22]([O-:24])=[O:23]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 86633656(1Z)-3-imino-3-(3-methyl-4-nitrophenyl)-1-[2-(propyloxy)phenyl]prop-1-en-1-amine

생성물 1

HCID 666728364-(3-methyl-4-nitrophenyl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one수율 81%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
75 °C

실험 절차

To a solution of (1Z)-3-imino-3-(3-methyl-4-nitrophenyl)-1-[2-(propyloxy)phenyl]prop-1-en-1-amine (2.20 g, 6.45 mmol) in ethanol (100 mL) was added urea (6.0 g, 100 mmol) and hydrochloric acid in dioxane 4.0 N (25 mL) at room temperature. The reaction mixture was heated to 75° C. for 16 h, at which time it was concentrated in vacuo, diluted with water (200 mL) and adjusted to pH 10 with sodium hydroxide 2.0 N. The product was extracted with chloroform (200 mL) then diluted with hexanes (50 mL) to precipitate the product. The solid was filtered and washed with chloroform/hexanes (1:4) to give 4-(3-methyl-4-nitrophenyl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one (1.80 g, 81%). MS (EI) for C20H19N4O3: 363 (MH+).

후처리

  1. concentrationwas concentrated in vacuo
  2. additiondiluted with water (200 mL)
  3. extractionThe product was extracted with chloroform (200 mL)
  4. additionthen diluted with hexanes (50 mL)
  5. customto precipitate the product
  6. filtrationThe solid was filtered
  7. washwashed with chloroform/hexanes (1:4)

출처 및 근거

ORD 기록
ord-a63ac55ff73c4f5696ae17ada3fb06a1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101625B2

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