Formaldehyde → HCID 22558209, compound

HRID 1267262Notes

Reaction equation

HRID 1267262 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-5044e43d560d4f679a7375fe7d728f63
Source dataset
uspto-grants-2003_04
Patent number
US06552057B2

Reaction notes

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