Acetic Acid → HCID 178491357, compound

HRID 447919

Reaction equation

HRID 447919 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:4]=1[CH2:5][NH:6][C:7](=[NH:12])[NH:8][C:9]([NH2:11])=[S:10].[F:19][C:20]([F:32])([F:31])[C:21]1[CH:30]=[CH:29][C:24]([C:25](=O)[CH2:26]Br)=[CH:23][CH:22]=1.C(O)(=O)C>O1CCOCC1>[CH3:18][O:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:5][NH:6][C:7]([NH:8][C:9]1[S:10][CH:26]=[C:25]([C:24]2[CH:29]=[CH:30][C:21]([C:20]([F:19])([F:31])[F:32])=[CH:22][CH:23]=2)[N:11]=1)=[NH:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 178491371HCID 178491371, compound

Product 1

HCID 178491357HCID 178491357, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Preparation took place analogously to Example 3 by reaction of 140 mg (0.52 mmol) N-[[(2,6-dimethoxybenzyl)amino](imino)methyl]thiourea with 140 mg (0.52 mmol) 4-(trifluoromethyl)phenacyl bromide. The educts were suspended in 3 ml dioxane, were added to 0.3 ml acetic acid and were heated for 40 minutes in the microwave (radiation 300 Watt). The mixture was subsequently concentrated and the crude product obtained was purified by chromatography on silica gel (dichloromethane/methanol 1-4%). Stirring of the yellow foam obtained with methyl tert.-butyl ether yielded 120 mg of a white amorphous solid.

Workup

  1. customPreparation
  2. temperaturewere heated for 40 minutes in the microwave (radiation 300 Watt)
  3. concentrationThe mixture was subsequently concentrated
  4. customthe crude product obtained
  5. customwas purified by chromatography on silica gel (dichloromethane/methanol 1-4%)
  6. customobtained with methyl tert.-butyl ether

Sources & evidence

ORD record
ord-9072fbad3f304c2c9ddca3e721445ed0
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Linked notes

Loading…