Water → 4,4'-Dichloro-2'-methylbenzanilide

HRID 1016646Notes

Reaction equation

HRID 1016646 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([CH3:19])[CH:13]=1.C(N(CC)CC)C.O>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][C:14]=2[CH3:19])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72514-Chloro-2-toluidineHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chloride

Product 1

HCID 2952414,4'-Dichloro-2'-methylbenzanilideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chlorobenzoyl chloride (19.5 g, 111 mmol) was added over 10 min. to a stirred, cooled (0° C.) solution of 4-chloro-2-methylaniline (15 g, 106 mmol) and triethylamine (22.2 mL, 16.1 g, 159 mmol) in dichloromethane (300 mL) and the mixture was stirred at room temperature for 2 h. Water (100 mL) was added and the dichloromethane was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate (saturated, 200 mL), water (200 mL) and ethyl acetate (1000 mL) were added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with ether and the solid was collected and dried in vacuo to give the title compound (27.3 g, 92%). 1H NMR (360 MHz, CDCl3) δ 7.82 (3H, m), 7.79 (1H, br s), 7.48 (2H, d, J 8.5 Hz), 7.23 (2H, m), and 2.30 (3H, s).

Workup

  1. customthe dichloromethane was evaporated under reduced pressure
  2. additionAqueous sodium hydrogen carbonate (saturated, 200 mL), water (200 mL) and ethyl acetate (1000 mL) were added
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with ether
  7. customthe solid was collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-175a1f612a8a4c78aac9bb2b4b160f6e
Source dataset
uspto-grants-2002_11
Patent number
US06476045B2

Reaction notes

Loading…