Triethylamine → N-{4-[3-(4-pentafluorosulphanyl-benzyl)-thioureidomethyl]-2-fluoro-phenyl}-methane sulphonamide

HRID 1670447

Reaction equation

HRID 1670447 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([F:14])[CH:4]=1.C(N(CC)CC)C.[F:22][S:23]([F:37])([F:36])([F:35])([F:34])[C:24]1[CH:33]=[CH:32][C:27]([CH2:28][N:29]=[C:30]=[S:31])=[CH:26][CH:25]=1>CN(C)C=O>[F:22][S:23]([F:34])([F:35])([F:36])([F:37])[C:24]1[CH:25]=[CH:26][C:27]([CH2:28][NH:29][C:30](=[S:31])[NH:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([F:14])[CH:4]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21097526N-(4-(aminomethyl)-2-fluorophenyl)methanesulfonamideHCID 866306334-(Pentafluorosulphanyl)benzylisothiocyanate

Product 1

HCID 16097202N-{4-[3-(4-pentafluorosulphanyl-benzyl)-thioureidomethyl]-2-fluoro-phenyl}-methane sulphonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-(4-aminomethyl-2-fluoro-phenyl)-methane sulphonamide (237 mg, 1.09 mmol) was dissolved in dimethylformamide (1 ml) and to this was added triethylamine (132 mg, 1.30 mmol) and 4-(pentafluorosulphanyl)benzylisothiocyanate (300 mg, 1.09 mmol) dissolved in dimethylformamide (1 ml). The reaction mixture was stirred over night at room temperature, the solvent removed under vacuum and the residue dissolved in a little methanol. Following column chromatographic cleaning (silica gel, hexane/ethyl acetate 1:5), the product was obtained as a solid (305 mg, 57% of the theoretical amount).

Workup

  1. customthe solvent removed under vacuum
  2. dissolutionthe residue dissolved in a little methanol
  3. customthe product was obtained as a solid (305 mg, 57% of the theoretical amount)

Sources & evidence

ORD record
ord-5f635046761445698db3a187c64b2c9c
Source dataset
uspto-grants-2011_08
Patent number
US07994167B2

Linked notes

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