Hydrochloric Acid → HCID 9890786, compound

HRID 263533Notes

Reaction equation

HRID 263533 reaction equation
[OH:1][N:2]([CH2:6][C:7]1[CH:30]=[CH:29][C:10]([O:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([OH:28])[C:25]([NH2:27])=[O:26])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)[C:3]([NH2:5])=[O:4].[OH-].[Na+].Cl[C:34](OCC)=[O:35].Cl.[O:40]1CCC[CH2:41]1>>[O:26]=[C:25]1[NH:27][C:34](=[O:35])[O:28][N:24]1[CH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15]/[CH:14]=[CH:13]\[CH2:12][O:11][C:10]2[CH:29]=[CH:30][C:7]([CH2:6][N:2]3[C:3](=[O:4])[NH:5][C:41](=[O:40])[O:1]3)=[CH:8][CH:9]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 86751011HCID 86751011, compound

Product 1

HCID 9890786HCID 9890786, compound

Procedure

To the solution of (Z)-1,4-Bis[4-[(1-hydroxyureido)methyl]phenoxy]-2-butene (0.75 g) in tetrahydrofuran (20 ml) was added 2N sodium hydroxide aqueous solution (6.9 ml) and then, with ice-cooling, ethyl chloroformate (0.66 ml) was added dropwise to the mixture. After 49 hours of stirring at room temperature, the reaction mixture was adjusted to pH 1 with 6N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate and then the solvent was evaporated under a reduced pressure. The resulting residue was subjected to silica gel column chromatography with chloroform-methanol (10:1) elution, and the obtained crude product was recrystallized from methanol to obtain (Z)-1,4-bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]-2-butene (0.31 g).

Workup

  1. temperaturewith ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography with chloroform-methanol (10:1) elution
  7. customthe obtained crude product
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-48d4f1e3228c49d8a48a8c02542113ba
Source dataset
uspto-grants-1997_07
Patent number
US05643931

Reaction notes

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