Water → N-(3-isopropyl-phenyl)-4-methyl-3-nitro-benzamide

HRID 883039Notes

Reaction equation

HRID 883039 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].O.[CH:15]([C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1)([CH3:17])[CH3:16]>C1COCC1>[CH:15]([C:18]1[CH:19]=[C:20]([NH:24][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[CH:21]=[CH:22][CH:23]=1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 4586793-Isopropylaniline

Product 1

HCID 26177932N-(3-isopropyl-phenyl)-4-methyl-3-nitro-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-3-nitro-benzoyl chloride (2.00 g, 0.010 mol) in THF (30 mL), in a water bath-cooled 100 mL RBF, was added 3-isopropyl-phenylamine (1.35 g, 0.010 mol) dropwise. The reaction was allowed to stir at room temperature for 1 hour before being concentrated. The mixture was taken up in EtOAc and washed with NaHCO3 (aq., conc.) and then brine. The solution was dried over MgSO4, filtered, and concentrated to yield N-(3-isopropyl-phenyl)-4-methyl-3-nitro-benzamide as an orange oil that solidifies upon standing. MS m/z 299=[M+H]+. Calc'd for C17H18N2O3: 298.34.

Workup

  1. concentrationbefore being concentrated
  2. washwashed with NaHCO3 (aq., conc.)
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-183053dcd2b140dabc62b9d48121d86c
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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