Formaldehyde → HCID 21055155, compound

HRID 558277Notes

Reaction equation

HRID 558277 reaction equation
[CH2:1]=O.[NH:3]1[CH2:6][CH:5]([N:7]2[C:11]([CH2:12][CH3:13])=[C:10]([O:14][C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)[C:9]([CH2:23][CH3:24])=[N:8]2)[CH2:4]1>C(O)=O.C(OCC)(=O)C>[Cl:22][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([Cl:21])[CH:18]=1)[O:14][C:10]1[C:9]([CH2:23][CH3:24])=[N:8][N:7]([CH:5]2[CH2:6][N:3]([CH3:1])[CH2:4]2)[C:11]=1[CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 9949815HCID 9949815, compound

Product 1

HCID 21055155HCID 21055155, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Paraformaldehyde (30 mg, 0.330 mmol) was added in one portion to a stirred solution of the pyrazole of Example 51 (120 mg, 0.330 mmol) in formic acid (2 ml) at room temperature. The mixture was heated at 100° C. for 5 hours, cooled to room temperature and concentrated under reduced pressure to leave a colourless oil. The oil was dissolved in ethyl acetate (50 ml) and the resulting solution was washed with saturated aqueous sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume) to provide the title compound (85 mg) as a colourless oil.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto leave a colourless oil
  4. washthe resulting solution was washed with saturated aqueous sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume)

Sources & evidence

ORD record
ord-1d8d81acd75940908208c9c8f6b9b46f
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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