1,1,1-Trifluoro-2,4-pentanedione → HCID 19813653, compound

HRID 1089381Notes

Reaction equation

Cl.[F:2][C:3]([F:15])([F:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([NH2:13])=[NH2+:12].CC(C)([O-])C.[K+].[F:22][C:23]([F:31])([F:30])[C:24]([CH2:26][C:27](=O)[CH3:28])=O>O1CCCC1>[CH3:28][C:27]1[CH:26]=[C:24]([C:23]([F:31])([F:30])[F:22])[N:13]=[C:11]([NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([F:14])([F:15])[F:2])[N:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 24 g (0.1 mole) of 2-trifluoromethylphenyl-guanidinium hydrochloride in 80 ml of tetrahydrofuran is added to a solution of 12 g (0.1 mole) of potassium tert.-butoxide in 100 ml of tetrahydrofuran. When the exothermic reaction has subsided, 15.4 g (0.1 mole) of α,α,α-trifluoroacetylacetone in 20 ml of tetrahydrofuran are added. The reaction mixture is stirred for 2 hours at 60° C., then concentrated by evaporation in a rotary evaporator. The residue is chromatographed on silica gel with a mixture of ethyl acetate and hexane (ratio 1:2). 18.7 g (58 2% of the theoretical amount) of the title compound of formula ##STR16## are obtained in the form of crystals having a melting point of 65°-66° C. (Comp. No. 2.020).

Workup

customWhen the exothermic reaction
concentrationconcentrated by evaporation in a rotary evaporator
customThe residue is chromatographed on silica gel with a mixture of ethyl acetate and hexane (ratio 1:2)

Sources & evidence

ORD record: ord-2a7c365fc8d74a8d89fba29384afbf8e
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04966622

Reaction notes

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