Water → 1,9-Bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]nonane

HRID 263534

反応式

HRID 263534 の反応式
[OH:1][NH:2][CH2:3][C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][NH:26][OH:27])=[CH:21][CH:20]=2)=[CH:6][CH:5]=1.C(O[C:33]([N:35]=[C:36]=[O:37])=[O:34])C.[OH-].[Na+].O.[O:41]1[CH2:45]CCC1.C[N:47](C)[CH:48]=[O:49]>>[O:49]=[C:48]1[NH:47][C:45](=[O:41])[O:27][N:26]1[CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][N:2]3[C:36](=[O:37])[NH:35][C:33](=[O:34])[O:1]3)=[CH:29][CH:28]=2)=[CH:24][CH:23]=1

参加物

6

反応物 5

HCID 962WaterHCID 14798Sodium HydroxideHCID 300166ethyl N-carbonylcarbamateHCID 19038524HCID 19038524、化合物HCID 21974620tetrahydrofuran N,N-dimethylformamide

生成物 1

HCID 190384571,9-Bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]nonane

実験手順

1,9-Bis[4-(hydroxyaminomethyl)phenoxy]nonane (1.07 g) was dissolved in 75 ml of tetrahydrofuran-dimethylformamide (4:1) and, in an atmosphere of argon and with ice-cooling, 0.75 ml of ethoxycarbonyl isocyanate was added dropwise to the solution. After 10 minutes of stirring, 1N sodium hydroxide aqueous solution was added dropwise to the reaction mixture with water-cooling, followed by 2 hours of stirring at room temperature. The solvent was evaporated under a reduced pressure, and the thus obtained residue was mixed with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride aqueous solution in that order and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under a reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the thus obtained 0.78 g of crude product obtained from fractions of chloroform-methanol (40:1) elution was recrystallized from methanol to obtain 0.69 g of 1,9-bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]nonane.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. waitfollowed by 2 hours
  4. stirringof stirring at room temperature
  5. customThe solvent was evaporated under a reduced pressure
  6. additionthe thus obtained residue was mixed with 1N hydrochloric acid
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated sodium chloride aqueous solution in that order
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThen, the solvent was evaporated under a reduced pressure
  11. customthe thus obtained 0.78 g of crude product obtained from fractions of chloroform-methanol (40:1) elution
  12. customwas recrystallized from methanol

出典と根拠

ORDレコード
ord-ac46ca30274b4a49b33f2170f1560a05
出典データセット
uspto-grants-1997_07
特許番号
US05643931

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