Dimethylamine → 1-(6-Chloro-3-pyridylmethyl)amino-1-dimethylamino-4,4,4-trifluoro-1-buten-3-one

HRID 483352Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](SC)=[CH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.[CH3:20][NH:21][CH3:22]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([N:21]([CH3:22])[CH3:20])=[CH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The product of Example 6, 1-(6-chloro-3-pyridylmethyl) amino-1-methylthio-4,4,4-trifluoro-1-buten-3-one, (2.0 g, 0.0065 mol) and dimethylamine (1.5 ml) were dissolved in ethanol (15 ml). The resulting solution was heated under reflux for 2 hours. The resulting mixture was cooled to ambient temperature (20° C.) and solvent removed by evaporation under reduced pressure. The solid residue was recrystallized from ether to give the product, 1-(6-chloro-3-pyridylmethyl)amino-1-dimethylamino-4,4,4-trifluoro-1-buten-3-one, in a yield of 0.3 g (16%), melting point 85° C.

Workup

temperatureThe resulting solution was heated
temperatureunder reflux for 2 hours
customremoved by evaporation under reduced pressure
customThe solid residue was recrystallized from ether

Sources & evidence

ORD record: ord-ba9b3b9e46e3415e953d4b033021f468
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05225423

Reaction notes

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