Methanol → 6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 8781

반응식

HRID 8781 반응식
CN(C)[CH:3]=[C:4]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=O.[C:23]([CH2:25][C:26]([NH2:28])=[O:27])#[N:24].CO.[H-].[Na+]>CN(C=O)C>[Cl:14][C:8]1[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[C:5]1[NH:28][C:26](=[O:27])[C:25]([C:23]#[N:24])=[CH:3][C:4]=1[C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 670199243-Dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one

생성물 1

HCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
95 °C

실험 절차

A solution of 3-dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one (14.4 mmol assumed) from Step A, cyanoacetamide (1.33 g, 15.8 mmol), and methanol (1.3 mL, 32 mmol) in DMF (35 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil) (1.45 g, 36 mmol) in DMF (16 mL) at rt. After the slow addition was complete, the reaction was heated to 95° C. for 2.5 h. Most of the DMF was then removed in vacuo before the reaction was diluted with aqueous 18% citric acid solution. The mixture was extracted twice with methylene chloride and the organic layers were washed with a portion of brine. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The solid residue was triturated with ether, filtered, and air dried to afford the product. HPLC/MS: 375 (M+1), 377 (M+3); Rt=3.47 min; 1H NMR (CDCl3): δ 6.96 (br d, J=8.4 Hz,2H), 7.14 (d, J=8.2 Hz, 1H), 7.25 (br d, J=8.4 Hz, 2H), 7.31 (dd, J=1.9 and 8.2 Hz, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.996 (s, 1H).

후처리

  1. additionAfter the slow addition
  2. customMost of the DMF was then removed in vacuo before the reaction
  3. additionwas diluted with aqueous 18% citric acid solution
  4. extractionThe mixture was extracted twice with methylene chloride
  5. washthe organic layers were washed with a portion of brine
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe solid residue was triturated with ether
  9. filtrationfiltered
  10. customair dried
  11. customto afford the product

출처 및 근거

ORD 기록
ord-69b20dddb4ce4c1fbef670bef6b342b4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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