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

HRID 660897
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HRID 660897 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ce60cd0e97464195a4e4f5720dfa1e6c
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084481B2

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