Methylamine → N,3,5-Trimethyl-4-nitrobenzamide

HRID 471446Notes

Reaction equation

HRID 471446 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].[C:15](N1C=CN=C1)([N:17]1C=CN=C1)=O.CN>O1CCCC1>[N+:11]([C:10]1[C:2]([CH3:1])=[CH:3][C:4]([C:5]([NH:17][CH3:15])=[O:6])=[CH:8][C:9]=1[CH3:14])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2494133,5-Dimethyl-4-nitrobenzoic acid

Product 1

HCID 86697180N,3,5-Trimethyl-4-nitrobenzamideYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethyl-4-nitrobenzoic acid (1 g, 5.12 mmol) is suspended in dry tetrahydrofuran (10 mL) and 1,1′-carbonyldiimidazole (0.91 g, 5.64 mmol) is added. The mixture is stirred for 3 hours then methylamine (2 M solution in tetrahydrofuran, 7.7 mL, 15.4 mmol) is added and the mixture stirred for 30 minutes. The solvent is removed, the residue suspended in EtOAc and washed with 0.2 M aqueous HCl solution, saturated sodium bicarbonate solution and brine, dried and the solvent removed under vacuum to give the title compound (Yield 1.0 g).

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. customThe solvent is removed
  3. washwashed with 0.2 M aqueous HCl solution, saturated sodium bicarbonate solution and brine
  4. customdried
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-bae357b2dc764c9784bdaee60752b42f
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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