Diphosgene → HCID 59699561, 화합물

HRID 901237노트

반응식

HRID 901237 반응식
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[CH3:9][O:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][NH:16][C:17]2[N:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1>O1CCOCC1>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[C:17]3[N:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[O:20][C:2]2=[O:3])=[CH:26][CH:27]=1

참가 물질

4

반응물 2

HCID 10426DiphosgeneHCID 23856703HCID 23856703, 화합물

생성물 1

HCID 59699561HCID 59699561, 화합물수율 67.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Trichloromethyl chloroformate (3.36 mL, 27.8 mmol) was added slowly to a suspension of 2-(4-methoxy-benzylamino)-nicotinic acid (11) (6 g, 23.23 mmol) in dioxane and refluxed for 18 h under nitrogen atmosphere. The solution was cooled and the solvent was removed under vacuum. The residue was dissolved in dichloromethane and washed by saturated NaHCO3 solution. The organic phase was dried over Na2SO4 and evaporated to yield a residue. The residue was recrystallized by ether to yield 4.47 g (67%) of 1-(4-methoxy-benzyl)-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione (12) as white solids. MP: 160° C.; 1H-NMR (DMSO-d6): δ 3.71 (s, 1H), 5.27 (s, 2H), 6.85 (d, J=7.0 Hz, 2H), 7.33 (m, 3H), 8.40 (dd, J=1.5, 7.5 Hz, 1H), 8.75 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 286 (M+23).

후처리

  1. temperaturerefluxed for 18 h under nitrogen atmosphere
  2. temperatureThe solution was cooled
  3. customthe solvent was removed under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed by saturated NaHCO3 solution
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated
  8. customto yield a residue
  9. customThe residue was recrystallized by ether

출처 및 근거

ORD 기록
ord-24b772d54e4f4305bbc1187dd5c7df86
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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