Triethylamine → HCID 178439130, compound

HRID 83854Notes

Reaction equation

HRID 83854 reaction equation
Br.[NH2:2][CH2:3][C:4](=O)[C:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)([CH3:7])[CH3:6].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[S:26])=[CH:20][CH:19]=1.CCN(CC)CC>C1C=CC=CC=1>[Cl:15][C:10]1[CH:9]=[C:8]([C:5]([C:4]2[N:24]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)[C:25]([SH:26])=[N:2][CH:3]=2)([CH3:7])[CH3:6])[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152414-Fluorophenyl isothiocyanateHCID 667410091-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide

Product 1

HCID 178439130HCID 178439130, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide (900 mg, 2.75 mmol), 4-fluorophenyl isothiocyanate (464 mg, 3.029 mmol), and Et3N (570 uL, 4.13 mmol) in dry benzene (20 mL) was heated at reflux 6 h. The reaction mixture was concentrated under reduced pressure, diluted with acetic acid (9 mL) and then heated at reflux 5 h. After cooling to room temperature and concentrating, the crude product was purified by flash column chromatography to afford 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (370 mg). 1H NMR (400 MHz, CDCl3) δ 7.15 (m, 2H), 6.91 (m, 2H), 6.80 (m, 2H), 6.62 (m, 2H), 1.61 (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux 6 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with acetic acid (9 mL)
  5. temperatureheated
  6. temperatureat reflux 5 h
  7. concentrationconcentrating
  8. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-72ab3983319c498288fd9cded17ad724
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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