Formic Acid → HCID 23368487, compound

HRID 1901615Notes

Reaction equation

HRID 1901615 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.CN(C)C=O.[NH2:16][CH:17]([CH2:30][O:31][CH3:32])[CH2:18][O:19][C:20]1[C:24]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=2[O:22][N:21]=1>C(OCC)(=O)C.O>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]2[O:22][N:21]=[C:20]([O:19][CH2:18][CH:17]([NH:16][CH:1]=[O:3])[CH2:30][O:31][CH3:32])[C:24]=2[CH:25]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 23368365HCID 23368365, compound

Product 1

HCID 23368487HCID 23368487, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 0.29 ml of formic acid is added 0.74 ml of acetic anhydride, and they are subjected to reaction at 40° C. for one hour. To the reaction mixture are added 5 ml of N,N-dimethylformamide and 1.00 g of 3-(2-amino-3-methoxypropoxy)-5-chloro-1,2-benzoisoxazole, and they are subjected to reaction at the same temperature for one hour. To the reaction mixture are added water and ethyl acetate, and after shaking, the organic layer is separated. Water is added again to the separated organic layer and the pH is adjusted to 8 with an aqueous sodium hydroxide solution, after which the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. Upon recrystallization from a mixed solvent of diisopropyl ether and ethyl acetate, there is obtained 0.50 g of colorless, crystalline 5-chloro-3-(2-formylamino-3-methoxypropoxy)-1,2-benzoisoxazole having a melting point of 90°-92° C.

Workup

  1. customare subjected to reaction at 40° C. for one hour
  2. customare subjected to reaction at the same temperature for one hour
  3. customthe organic layer is separated
  4. additionWater is added again to the separated organic layer
  5. customafter which the organic layer is separated
  6. washThe separated organic layer is washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customafter which the solvent is removed by distillation under reduced pressure
  9. customUpon recrystallization from a mixed solvent of diisopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-e84bb2536af44b76af25a339c0b52886
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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