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Oxalic Acid → 7-Chloro-2,3-dihydro-4-methyl-2-[2-methyl(phenylmethyl)amino]pyrido[3,2-f][1,4]oxazepin-5(4H)-one oxalate

HRID 4864
ノート
印刷プレビュー

反応式

HRID 4864 の反応式
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8](CCCl)[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH2:18]([CH2:25][NH2:26])[C:19]1C=C[CH:22]=[CH:21][CH:20]=1.[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>C(O)C.C(O)(C)C>[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([NH:26][CH2:25][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:27]=3[CH3:28])[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 971Oxalic AcidHCID 1001Phenethylamine2 回HCID 137264457-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one

生成物 1

HCID 212715447-Chloro-2,3-dihydro-4-methyl-2-[2-methyl(phenylmethyl)amino]pyrido[3,2-f][1,4]oxazepin-5(4H)-one oxalate収率 47.9%

試薬・触媒・溶媒 2

HCID 702Ethanol
溶媒
HCID 3776Isopropanol溶媒

実験手順

To a solution of 6.0 g (0.022 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 5.3 g (0.044 mole) of benzylmethylamine and the mixture heated to reflux for three days. The solvent was removed by rotary evaporation, and the residue was taken up in 100 ml of methylene chloride, which was subsequently washed with 2×50 ml of dilute sodium hydroxide and 50 ml water, dried over sodium sulfate, filtered, and concentrated by rotary evaporation. Residual benzylmethylamine was removed at 95° C., 0.5 mm Hg. However, the mass spectrum now showed starting material; therefore, the residue was taken up in 50 ml of absolute ethanol. To the resulting solution was added 2.7 g (0.022 mole) of benzylmethylamine and the mixture heated to reflux for 24 hrs. The reaction mixture was subjected to the same work-up as mentioned before. The syrup was treated with oxalic acid in isopropyl alcohol. The resulting crystals were recrystallized from ethanol/isopropyl alcohol to give 4.7 g (47.9%) of white crystals, m.p. 176°-179° C.

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux for three days
  3. customThe solvent was removed by rotary evaporation
  4. washwhich was subsequently washed with 2×50 ml of dilute sodium hydroxide and 50 ml water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customResidual benzylmethylamine was removed at 95° C.
  9. temperaturethe mixture heated
  10. temperatureto reflux for 24 hrs
  11. customThe resulting crystals were recrystallized from ethanol/isopropyl alcohol

出典と根拠

ORDレコード
ord-c3bc64bc129e484f957dfe469d616691
出典データセット
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04727152

反応ノート

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