tert-Butylsulfinamide, (R)-(+)- → (NZ)-2-methyl-N-[[2-(trifluoromethyl)pyrimidin-5-yl]methylidene]propane-2-sulfinamide

HRID 592284Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][N:4]=1.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>ClC(Cl)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:13][C:14]([S:17](/[N:19]=[CH:9]\[C:6]1[CH:5]=[N:4][C:3]([C:2]([F:12])([F:11])[F:1])=[N:8][CH:7]=1)=[O:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(trifluoromethyl)pyrimidine-5-carbaldehyde (27.2 g, 99 mmol) in dichloroethane (250 mL) was added (R)-(+)-2-methyl-2-propanesulfinamide (13.3 g, 109.0 mmol) and copper(II) sulfate (31.5 g, 197.0 mmol). The mixture was heated to 50° C. After 18 h, the mixture was cooled to ambient temperature and filtered through a pad of silica gel. The filtered cake was washed with dichloromethane and the filtrate was concentrated to give the title compound (27.3 g). MS 224 [(M+1)-56].

Workup

temperaturethe mixture was cooled to ambient temperature
filtrationfiltered through a pad of silica gel
washThe filtered cake was washed with dichloromethane
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-7c4af7ccee1c4865b328fd0603dd5b2c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238647B2

Reaction notes

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