Triethylamine → 1-(3-(4-Fluoro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)thiourea

HRID 83864

Reaction equation

HRID 83864 reaction equation
Cl.[NH2:2][CH2:3][C:4](=[O:17])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][CH3:16])[CH:9]=1)([CH3:7])[CH3:6].[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1.CCN(CC)CC>C(Cl)Cl>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]([CH3:7])([CH3:6])[C:4](=[O:17])[CH2:3][NH:2][C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[S:27])=[CH:9][C:10]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152414-Fluorophenyl isothiocyanateHCID 667407491-Amino-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one hydrochloride

Product 1

HCID 866622481-(3-(4-Fluoro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)thioureaYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-amino-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one hydrochloride (35.4 g, 0.135 mol) and 4-fluorophenyl isothiocyanate (21.75 g, 0.142 mol) in DCM (500 mL) was added Et3N (37.6 ml, 0.27 mol) at 0° C., and the reaction mixture was warm to room temperature over 1 h. The reaction mixture was washed with 1N HCl (500 mL), satd NaHCO3 (500 mL) and brine (500 mL) successively, dried over MgSO4, filtered and concentrated under reduced pressure give a residue, which was triturated with Hex-EtOAc to afford 1-(3-(4-fluoro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)thiourea (45 g, 88%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.85 (b, 1H), 7.25 (m, 2H), 7.15 (m, 2H), 7.05 (m, 1H), 6.79 (m, 2H), 6.67 (b, 1H), 3.88 (s, 3H), 1.54 (s, 6H).

Workup

  1. washThe reaction mixture was washed with 1N HCl (500 mL), satd NaHCO3 (500 mL) and brine (500 mL) successively
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customgive a residue, which
  6. customwas triturated with Hex-EtOAc

Sources & evidence

ORD record
ord-b3658da31f504270aa4d653082b954bd
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Linked notes

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