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

HRID 422046ノート

反応式

HRID 422046 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
75 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-a63ac55ff73c4f5696ae17ada3fb06a1
出典データセット
uspto-grants-2012_01
特許番号
US08101625B2

反応ノート

読み込み中…