Acetic Acid → HCID 59637296, compound

HRID 2047424Notes

Reaction equation

HRID 2047424 reaction equation
[NH2:1][N:2]1[C:6]([CH2:7][NH:8]C(=O)OC(C)(C)C)=[CH:5][C:4]([C:16]([F:19])([F:18])[F:17])=[N:3]1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=O.C(O)(=O)C.C(OCC)(=O)C.CCCCCC>CO>[NH2:8][CH2:7][C:6]1[N:2]([NH:1][CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)[N:3]=[C:4]([C:16]([F:17])([F:18])[F:19])[CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 142732-PyridinecarboxaldehydeHCID 21226206Ethyl acetate hexaneHCID 59637266HCID 59637266, compound

Product 1

HCID 59637296HCID 59637296, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of tert-butyl (1-amino-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (2 g, 0.0071 mol) in methanol (15 ml), picolinaldehyde (1.14 g (1 ml), 0.016 mol, 1.5 eq) taken in methanol (5 ml) was added. Then the reaction mixture was acidified with acetic acid (0.2 ml, catalytic) and heated to reflux for 24 hrs. Progress of the reaction was monitored by TLC (10% ethyl acetate/hexane, Rf˜0.4). On completion of the reaction, methanol was distilled off completely. Residue was taken in ice water (200 ml) and the product extracted with ethyl acetate (4×50 ml). Combined extract was washed with water (2×50 ml), dried over sodium sulfate and the ethyl acetate was distilled off completely. Crude obtained was recrystalised from hexane (10 ml) to yield the required product as liquid (2 g, 76% yield).

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureto reflux for 24 hrs
  4. distillationwas distilled off completely
  5. extractionthe product extracted with ethyl acetate (4×50 ml)
  6. extractionCombined extract
  7. washwas washed with water (2×50 ml)
  8. dry with materialdried over sodium sulfate
  9. distillationthe ethyl acetate was distilled off completely
  10. customCrude obtained
  11. customwas recrystalised from hexane (10 ml)

Sources & evidence

ORD record
ord-9694e59341f540cd8879fa1fa23d3a44
Source dataset
uspto-grants-2013_11
Patent number
US08592471B2

Reaction notes

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