Trifluoroacetic anhydride → HCID 809626, compound

HRID 362452Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][C:10]([CH3:14])=[N:9]2)=[CH:4][CH:3]=1.F[C:16](F)(F)[C:17](OC(=O)C(F)(F)F)=[O:18]>>[CH3:14][C:10]1[CH2:11][C:12](=[O:13])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:17](=[O:18])[CH3:16])=[CH:7][CH:6]=2)[N:9]=1

Participants

Reactant 2

HCID 9845Trifluoroacetic anhydride

HCID 808152-(4-Aminophenyl)-2,4-dihydro-5-methyl-3H-pyrazol-3-one

Product 1

HCID 809626HCID 809626, compoundYield 65%

Procedure

Yield: 1.5 g of N-(4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)phenyl)acetamide (65% of theory), oil obtained analogously from 2-(4-aminophenyl)-5-methyl-2,4-dihydro-3-pyrazolone and trifluoroacetic anhydride is N-(4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)-phenyl)trifluoroacetamide from 2-(3-aminophenyl)-5-methyl-2,4-dihydro-3-pyrazolone and trifluoroacetic anhydride is N-(3-(4,5-dihydro-3-methy-5-oxo-1H-pyrazol-1-yl)-phenyl)trifluoroacetamide from 2-(3-aminophenyl)-5-methyl-2,4-dihydro-3-pyrazolone and acetic anhydride is N-(3-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)-phenyl)acetamide from 5-methyl-2-(4-aminophenyl)-2,4-dihydro-3-pyrazolone (prepared in analogy to Example 10) and acetic anhydride is N-(4-(4,5-dihydro-3-methyl-5-oxo-5H-pyrazol-1-yl)-phenyl)acetamide and by reaction with 2-ethylaniline N-(4-(4-(2-ethylanilinomethylene)-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)phenyl)acetamide, m.p.: 230° C.

Sources & evidence

ORD record: ord-e51fd68feb6e4e6f981a975fdc5e91e1
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869516

Reaction notes

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