2-(3,4-Dichlorophenyl)ethanethioamide → Trifluoroacetic acid

HRID 505582Notes

Reaction equation

HRID 505582 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH2:12])=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]2)=[CH:19][CH:18]=1)=O.C(#N)C.O.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[CH2:9][C:10]1[S:11][CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[CH:21][CH:22]=2)[N:12]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]

Participants

6

Reactant 3

HCID 215042642-(3,4-Dichlorophenyl)ethanethioamideHCID 22145617Water TFA acetonitrileHCID 250673052-Bromo-1-[4-(4-methyl-1H-imidazol-1-yl)phenyl]ethan-1-one

Product 2

HCID 6422Trifluoroacetic acidHCID 589110272-(3,4-Dichloro-benzyl)-4-[4-(4-methyl-imidazole-1-yl)-phenyl]-thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The thioacetamide 1213 (0.08 mmol) and 2-bromo-1-[4-(4-methyl-imidazole-1-yl)-phenyl]-ethanone (0.08 mmol) 10 were dissolved in 1 ml DMF. The reaction was stirred at 70 C for 6 hours. After cooling to room temperature, the reaction mixture was directly injected into a reversed phase HPLC (Gilson 215) using acetonitrile/water/TFA gradient and C18 stationary phase to isolate and then concentrate to give the title product 1214 as a TFA salt.

Workup

  1. customC18 stationary phase to isolate
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-7b0a71bea2d041e481aa68e03df02b1b
Source dataset
uspto-grants-2010_08
Patent number
US07781442B2

Reaction notes

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