4-Methyl-3-nitrobenzoyl chloride → HCID 59346396, compound

HRID 1926689Notes

Reaction equation

HRID 1926689 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=2[C:17]([F:20])([F:19])[F:18])[CH2:5][CH2:4]1)[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][C:32]=1[N+:40]([O-:42])=[O:41]>ClCCl>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:31]([CH3:30])=[C:32]([N+:40]([O-:42])=[O:41])[CH:33]=3)=[CH:12][C:11]=2[C:17]([F:20])([F:18])[F:19])[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 591345644-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline

Product 1

HCID 59346396HCID 59346396, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a solution of 4-(4-Ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (8.0 g, 27.9 mmol, 1.0 eq.) in dichloromethane (140 ml) is added diisopropylethyl amine (5.27 ml, 30.69 mmol, 1.1 eq.). The solution is cooled to 0° C., after which 4-Methyl-3-nitrobenzoylchloride (4.18 ml, 28.73 mmol, 1.03 eq.) is added in portions into the reaction mixture which is further equilibrated for 30 minutes. The reaction mixture is then partitioned between dichloromethane and water. The organic layer is separated and the aqueous layer is extracted with dichloromethane. The combined organic extracts are washed with water, dried over Na2SO4, filtered and concentrated to afford the desired product which is used in the next step without further purification.

Workup

  1. customThe reaction mixture is then partitioned between dichloromethane and water
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with dichloromethane
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6aaee300388141ed964e8fdfb12c61f2
Source dataset
uspto-grants-2012_05
Patent number
US08183248B2

Reaction notes

Loading…