Acetonitrile → HCID 178506181, compound

HRID 2220870Notes

Reaction equation

HRID 2220870 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][NH2:7].[F:12][C:13]([F:27])([F:26])[C:14]1[CH:15]=[C:16]([N:20]=[C:21]([S-])[S-](C)C)[CH:17]=[CH:18][CH:19]=1.CC#N>CS(C)=O.C(O)(C(F)(F)F)=O>[N:3]1[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][NH:7][C:21]=1[NH:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:26])[F:27])[CH:15]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 1780962-(Aminomethyl)anilineHCID 178503842HCID 178503842, compound

Product 1

HCID 178506181HCID 178506181, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
190 °C

Procedure

Under an atmosphere of nitrogen, sodium hydroxide (0.1 ml, solution in water, 20 mol/l, 2 mmol) was added to a solution of 2-aminobenzylamine (92 mg, 0.75 mmol) in DMSO (1 ml). After 30 min, a solution of (3-trifluoromethyl-phenyl)-dimethyl-dithiocarbonimidate (200 mg, 0.75 mmol) in DMSO (1 ml) was added, and the mixture was heated to 190° C. for 3 h. The title compound (50 mg, 23%, MS: m/e=292.1 [M+H+]) was isolated from the reaction mixture by preparative, reverse phase HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

Sources & evidence

ORD record
ord-efc3365becc74a879d7331c0b7137304
Source dataset
uspto-grants-2008_05
Patent number
US07368454B2

Reaction notes

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