Dimethyl Sulfoxide → 2-[2-(1-Azetidinyl)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione fumarate

HRID 1981768

反応式

HRID 1981768 の反応式
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[C:17](=[O:20])([O-:19])[O-].[K+].[K+].[NH:23]1[CH2:26][CH2:25][CH2:24]1.CS(C)=[O:29]>>[C:6]([OH:29])(=[O:5])/[CH:7]=[CH:13]/[C:17]([OH:19])=[O:20].[N:23]1([CH2:2][CH2:3][CH:4]2[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]3[CH:13]=[CH:14][CH:15]=[N:16][C:6]=3[O:5]2)[CH2:26][CH2:25][CH2:24]1

参加物

5

反応物 4

HCID 679Dimethyl SulfoxideHCID 10422Azetidine3 回HCID 11430Potassium CarbonateHCID 137264422-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)thione

生成物 1

HCID 137265622-[2-(1-Azetidinyl)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione fumarate収率 31%

実験手順

To 5.0 g (0.0914 mole) of 2-(2-chloroethyl)-2,5-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione dissolved in 50 ml of dimethylsulfoxide was added 8.04 g (0.058 mole) of potassium carbonate and 1.21 g (0.021 mole) of azetidine. The reaction mixture was stirred at room temperature for 8 hr after which was added 0.5 g (0.009 mole) of azetidine and the mixture was stirred overnight at room temperature. An additional 0.3 g (0.005 mole of azetidine was added and stirring was continued for 24 hr. The mixture was filtered and solvent removed by rotary evaporator at 80° C., 0.5 mm Hg. The residue was taken up in 100 ml of chloroform and the solution was washed with two 30 ml portions of dilute aqueous sodium hydroxide. The organic layer was dried over magnesium sulfate, filtered and concentrated by rotary evaporator. The residue was reacted with fumaric acid in isopropyl alcohol to give 2.5 g (31%) of pale yellow crystals, m.p. 122°-126° C.

後処理

  1. stirringthe mixture was stirred overnight at room temperature
  2. stirringstirring
  3. waitwas continued for 24 hr
  4. filtrationThe mixture was filtered
  5. customsolvent removed by rotary evaporator at 80° C.
  6. washthe solution was washed with two 30 ml portions of dilute aqueous sodium hydroxide
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporator
  10. customThe residue was reacted with fumaric acid in isopropyl alcohol

出典と根拠

ORDレコード
ord-c0797511ebb44ff09ab87505635d5569
出典データセット
uspto-grants-1986_06
特許番号
US04592866

関連ノート

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