Diphosgene → HCID 59699561、化合物

HRID 901237ノート

反応式

HRID 901237 の反応式
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

参加物

4

反応物 2

HCID 10426DiphosgeneHCID 23856703HCID 23856703、化合物

生成物 1

HCID 59699561HCID 59699561、化合物収率 67.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-24b772d54e4f4305bbc1187dd5c7df86
出典データセット
uspto-grants-2008_04
特許番号
US07361760B2

反応ノート

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