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

HRID 263534Notes

Reaction equation

HRID 263534 reaction equation
[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

Participants

6

Reactant 5

HCID 962WaterHCID 14798Sodium HydroxideHCID 300166ethyl N-carbonylcarbamateHCID 190385241,9-Bis[4-(hydroxyaminomethyl)phenoxy]nonaneHCID 21974620tetrahydrofuran N,N-dimethylformamide

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ac46ca30274b4a49b33f2170f1560a05
Source dataset
uspto-grants-1997_07
Patent number
US05643931

Reaction notes

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