Potassium bisulfate → (S)-2-methyl-propane-2-sulfinic acid 1-pyrimidin-2-yl-methylideneamide

HRID 926371Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7]=O.[CH3:9][C:10]([S@@:13]([NH2:15])=[O:14])([CH3:12])[CH3:11].S([O-])(O)(=O)=O.[K+]>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7]=[N:15][S@:13]([C:10]([CH3:12])([CH3:11])[CH3:9])=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-pyrimidine-carboxaldehyde (11.5 g, 107 mmol), (S)-(−)-2-methyl-2-propanesulfinamide (12.9 g, 107 mmol) and potassium hydrogensulfate (14.5 g, 107 mmol) in toluene (57 ml) was heated at 50° C. overnight. After decanting the solution, the solid residue is washed 3 times with dichloromethane, the washings combined with the decanted solution and solvents are evaporated in vacuo to give 18.2 g (81%) of (S)-2-methyl-propane-2-sulfinic acid 1-pyrimidin-2-yl-methylideneamide. LC/MS (method 3): Rt=1.29 min; m/z=212.09 (M+H+).

Workup

customAfter decanting the solution
washthe solid residue is washed 3 times with dichloromethane
customare evaporated in vacuo

Sources & evidence

ORD record: ord-2e7e59752f8746ed947054f69feb5f9f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284333B2

Reaction notes

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