Triethylamine → N-Methyl-4-nitrobenzamide

HRID 1665633Notes

Reaction equation

HRID 1665633 reaction equation
Cl.CN.[CH2:4]([N:6](CC)CC)C.[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)([O-:13])=[O:12].C(OCC)(=O)C>CCCCCC>[CH3:4][NH:6][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 8857Ethyl AcetateHCID 6364545Methylamine hydrochloride

Product 1

HCID 347921N-Methyl-4-nitrobenzamideYield 89.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 40% aqueous solution of Methylamine hydrochloride (2.175 g, 33.2 mmol) and Triethyl amine (3.75 g, 37.18 mmol) at 0° C., added 4-Nitro-benzoyl chloride (4.6 g, 24.78 mmol) and stirred for 30 mins. The reaction was monitored by TLC (50% Ethyl acetate in Hexane). The solid precipitate so obtained was filtered, washed with ice cold water and dried to afford 4 g (89%) of N-Methyl-4-nitro-benzamide. 1H NMR: (DMSO-d6): δ 8.78 (s, 1H), 8.32 (d, 2H), 8.06 (d, 2H), 2.8 (s, 3H).

Workup

  1. customThe solid precipitate so obtained
  2. filtrationwas filtered
  3. washwashed with ice cold water
  4. customdried

Sources & evidence

ORD record
ord-ac064286d23f43c08a31da9d476eb79f
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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