Ethanol → HCID 9901849, compound

HRID 968375Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3](=O)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13].[C:17]1([NH:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)C>C(OCC)(=O)C>[C:17]1([N:23]2[CH:5]([C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=3[F:13])[CH2:4][C:3]([C:2]([F:16])([F:15])[F:1])=[N:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

In a 50 mL beaker are introduced (E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-buten-2-one(2.66 g, 11.2 mmol), monohydrated p-toluensulphonic acid (2.1 g, 11.2 mmol) and phenylhydrazine chlorhydrate (1.33 g, 12.3 mmol) and heated to 110° C. A small amount of ethyl alcohol can be used to facilitate the initial mixture. After approximately 2 h (control by CCF) the mixture is allowed to cool and it is diluted with ethyl acetate. It is then washed with a saturated solution of NaHCO3, dried with MgSO4, filtered and the solvent evaporated at low pressure. The crude thus obtained (3.9 g) is recrystallised with methanol (2 mL) to precipitate 3.67 g (65%) of the pyrazoline (±)-5: pf=83–84° C.; IR (KBr) μ max (cm−1) 1600, 1505, 1326; 1H-RMN (CDCl3) δ (ppm): 7.28–6.72 (m, 8H), 5.64 (dd, J=13 Hz, J=7.5 Hz, 1H), 3.8–3.6 (m, 1H), 2.94 (dd, J=17.2 Hz, J=7 Hz, 1H).

Workup

temperatureto cool
washIt is then washed with a saturated solution of NaHCO3
dry with materialdried with MgSO4
filtrationfiltered
customthe solvent evaporated at low pressure
customThe crude thus obtained (3.9 g)
customis recrystallised with methanol (2 mL)
customto precipitate 3.67 g (65%) of the pyrazoline
custompf=83–84° C.

Sources & evidence

ORD record: ord-e7a70f0c8b4a48dfba57e24b1030e889
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958403B2

Reaction notes

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