Toluene → N-[4-(1-Aminoethyl)-2-fluoro-6-vinylphenyl]methanesulfonamide

HRID 2358376Notes

Reaction equation

HRID 2358376 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[CH:15]=[C:14]([CH:16]=[CH2:17])[C:13]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[C:12]([F:23])[CH:11]=1)[CH3:9])(C)(C)C.C1(C)C=CC=CC=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][CH:8]([C:10]1[CH:15]=[C:14]([CH:16]=[CH2:17])[C:13]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[C:12]([F:23])[CH:11]=1)[CH3:9]

Participants

5

Reactant 2

HCID 1140TolueneHCID 68453629[1-(3-Fluoro-4-methanesulfonylamino-5-vinyl phenyl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68455310N-[4-(1-Aminoethyl)-2-fluoro-6-vinylphenyl]methanesulfonamideYield 134.2%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

[1-(3-fluoro-4-methanesulfonylamino-5-vinyl phenyl)ethyl]carbamic acid tert-butyl ester (0.06 mmol, 20.2 mg) was dissolved in methylene chloride, 5˜6 drops of CF3COOH were added. A reaction mixture was stirred for 12 hr. A toluene was added. The reaction mixture was concentrated in vacuo to yield brownish syrup (20.8 mg, 100.0%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-cb073f7511d04f34b05d8bfb1cf903e4
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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