Pyridine → 2-(4-Tert-butylbenzoylamino)-4-nitro-n-(4-methoxyphenyl)benzamide

HRID 395720Notes

Reaction equation

HRID 395720 reaction equation
[NH2:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5].N1C=CC=CC=1.[C:28]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29]>C(Cl)Cl>[C:28]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([NH:1][C:2]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=2[C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[O:5])=[O:37])=[CH:39][CH:40]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 105173792-Amino-N-(4-methoxyphenyl)-4-nitrobenzamide

Product 1

HCID 106232992-(4-Tert-butylbenzoylamino)-4-nitro-n-(4-methoxyphenyl)benzamideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-amino-4-nitro-N-(4-methoxyphenyl)benzamide (2.0 g, 7.0 mmol) and pyridine (0.62 mL, 7.7 mmol) in methylene chloride (40 mL) was added 4-tert-butylbenzoyl chloride (1.44 mL, 7.35 mmol). After stirring for 1.5 h, silica gel (30 g) was added and the solvent evaporated with a stream of nitrogen. The resulting material was chromatographed (silica gel, 5% hexanes/95% methylene chloride to 1.25% ethyl acetate/98.75% methylene chloride) to give 2.41 g (77%) of the title compound as a yellow solid; mp 221° C.

Workup

  1. additionsilica gel (30 g) was added
  2. customthe solvent evaporated with a stream of nitrogen
  3. customThe resulting material was chromatographed (silica gel, 5% hexanes/95% methylene chloride to 1.25% ethyl acetate/98.75% methylene chloride)

Sources & evidence

ORD record
ord-a4e0f03bca284404b759e5ddd643aa73
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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