2-Chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide → HCID 178492991, compound

HRID 83874Notes

Reaction equation

HRID 83874 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:26])([C:10](=O)[CH2:11][NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[S:14])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:27]([NH2:30])(=[O:29])=[O:28]>CC(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([O:23][CH3:24])[CH:17]=3)[C:13]([SH:14])=[N:12][CH:11]=2)([CH3:26])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:27]([NH2:30])(=[O:29])=[O:28]

Participants

3

Reactant 1

HCID 866622522-Chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide

Product 1

HCID 178492991HCID 178492991, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide (8.6 g, 18.1 mmol) in AcOH (100 mL) was refluxed 3 h. After the reaction was complete, the solution was cooled to room temperature and azeotroped with toluene. The residue was triturated with Et2O, filtered and dried to provide the title compound (6.8 g, 82% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3+MeOD) δ 7.92 (d, J=8.4 Hz, 1H), 7.09 (s, 1H), 7.06 (d, J=8.4 Hz, 1H), 6.97 (t, J=8.4 Hz, 1H), 6.89 (s, 1H), 6.38 (m, 1H), 6.13 (d, J=7.2 Hz, 1H), 3.58 (s, 3H), 1.54 (s, 6H); MS (EI) m/z 456 (MH+).

Workup

  1. customazeotroped with toluene
  2. customThe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-aac0b30e74a041b9b6bced49430c31a2
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…