Formaldehyde → HCID 22558209, compound

HRID 2270938Notes

Reaction equation

HRID 2270938 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.[CH2:19]=O>C(O)=O>[CH3:19][NH:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]2[N:6]=[C:7]([N:9]3[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]3)[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 12016519HCID 12016519, compound

Product 1

HCID 22558209HCID 22558209, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 50 mg portion of 6-amino-5-chloro-2-(4-methyl-1-piperazinyl)benzoxazole was dissolved in 5 ml of formic acid, and the solution was mixed with 3 ml of formaldehyde and stirred at room temperature for 3 hours. The solvent was concentrated under a reduced pressure, and the resulting oily matter was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate, and then the solvent was evaporated under a reduced pressure. Thereafter, the thus obtained mixture was purified by a silica gel column chromatography (chloroform:methanol=20:1) to obtain the title compound (28 mg) in light yellow color.

Workup

  1. concentrationThe solvent was concentrated under a reduced pressure
  2. additionthe resulting oily matter was mixed with saturated sodium bicarbonate aqueous solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThereafter, the thus obtained mixture was purified by a silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-87455482249549a9a6e3581900660818
Source dataset
uspto-grants-2001_12
Patent number
US06333328B1

Reaction notes

Loading…