Hydroxyamine hydrochloride → 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone

HRID 1463250

반응식

HRID 1463250 반응식
[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20]#[CH:21])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](C=O)[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].Cl.[NH2:24][OH:25]>C(O)C>[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20]#[CH:21])[C:6]([C:11]2[CH2:12][C:13](=[N:24][OH:25])[CH:14]=[CH:15][CH:16]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 196906845,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone

생성물 1

HCID 1363783855,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone수율 77.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a 100 mL RBF were charged 1.1 g (3.7 mmol) of 5,6-diethyl-2-(3-formyl-phenyl)-3-propargyl-4(3H)-pyrimidinone, 0.52 g (7.5 mmol) of hydroxylamine hydrochloride and 50 mL of ethanol. The reaction mixture was refluxed for 17 hours. The ethanol was removed in vacuo and ether and ethyl acetate were added to the residue. The organics were washed 3 times with water. The organic layer was gravity filtered to remove 0.22 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139). The organic layer was dried over MgSO4 and concentrated to yield a further 0.67 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139) as a white solid. A combined yield of 77.6% was obtained. 1H-NMR (CDCl3) 1.25(6H,m); 2.35(1H,t); 2.65(4H,m); 4.6(2H,d); 7.49-8.15(4H,m); 8.7 (1H,s)

후처리

  1. temperatureThe reaction mixture was refluxed for 17 hours
  2. customThe ethanol was removed in vacuo and ether and ethyl acetate
  3. additionwere added to the residue
  4. washThe organics were washed 3 times with water
  5. filtrationfiltered
  6. customto remove 0.22 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-aa0c2b053ed741ed99f555cebee6c877
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300477

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