Triethylamine → 2-(2-(4-Chloro-3-methoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)hydrazine carbothioamide

HRID 83934

Reaction equation

HRID 83934 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:15])([CH3:14])[C:10]([NH:12][NH2:13])=[O:11])=[CH:5][C:4]=1[O:16][CH3:17].[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>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:15])([CH3:14])[C:10]([NH:12][NH:13][C:26](=[S:27])[NH:25][C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[O:11])=[CH:5][C:4]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152414-Fluorophenyl isothiocyanateHCID 667408342-(4-Chloro-3-methoxyphenyl)-2-methylpropanehydrazide hydrochloride

Product 1

HCID 866622622-(2-(4-Chloro-3-methoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)hydrazine carbothioamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloro-3-methoxyphenyl)-2-methylpropanehydrazide hydrochloride (6.88 g, 0.02 mol) and 4-fluorophenylisothiocyanate (3.96 g, 0.03 mol, 1.05 eq.) in DCM (500 mL) at 0° C. was added Et3N (7 mL, 1.29 mol, 2.0 eq.) and the resulting solution was stirred for 1.5 h at room temperature. The reaction mixture was washed with 1M HCl, satd NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with DCM/Et2O, collected by filtration and dried to give 2-(2-(4-Chloro-3-methoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)hydrazine carbothioamide (8.13 g, 83% as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.32-7.30 (d, 1H), 7.25-7.22 (m, 2H), 7.01-7.05 (t, 2H), 6.95-6.94 (d, 1H), 6.93-6.90 (dd, 1H), 3.88 (s, 3H), 1.64 (s, 6H).

Workup

  1. washThe reaction mixture was washed with 1M HCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with DCM/Et2O
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-fb1356b07d30490999d41fd5d56501e7
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Linked notes

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