Formic Acid → Methyl[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

HRID 660897Notes

Reaction equation

HRID 660897 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]1[C:9](=[O:10])[N:8](CC=C)[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:6]1.C(O)=O.C(N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]1[C:9](=[O:10])[NH:8][C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:6]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 58012233Methyl [3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Product 1

HCID 136199105Methyl[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Under an argon atmosphere, 200 mg (0.65 mmol) of the compound from Example 214A, 49 μl of formic acid (1.3 mmol), 226 μl of triethylamine (1.63 mmol) and 38 mg of tetrakis(triphenylphosphine)palladium(0) (32 μmol) are dissolved in 2 ml degassed dioxan and stirred overnight at reflux temperature. To dissolve the precipitated solid, the reaction mixture is diluted with 20 ml of methanol after cooling to RT. The palladium catalyst is filtered off and the filtrate freed of the volatile components on the rotary evaporator. The residue is stirred with 5 ml acetonitrile and then suction-filtered. The solid is washed with acetonitrile and dried under high vacuum. It corresponds to the title compound with a purity of ca. 76% (130 mg, 57% of theory) and is used in the next reaction without further purification.

Workup

  1. customdegassed dioxan
  2. temperatureat reflux temperature
  3. dissolutionTo dissolve the precipitated solid
  4. additionthe reaction mixture is diluted with 20 ml of methanol
  5. filtrationThe palladium catalyst is filtered off
  6. customthe filtrate freed of the volatile components on the rotary evaporator
  7. stirringThe residue is stirred with 5 ml acetonitrile
  8. filtrationsuction-filtered
  9. washThe solid is washed with acetonitrile
  10. customdried under high vacuum
  11. customis used in the next reaction without further purification

Sources & evidence

ORD record
ord-ce60cd0e97464195a4e4f5720dfa1e6c
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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