Hydrochloric Acid → 3-(1-Cyano-1-methylethyl)-N-(4-methyl-3-nitro-phenyl)benzamide

HRID 1800724Notes

Reaction equation

HRID 1800724 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([C:14]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21])([CH3:16])[CH3:15])#[N:13].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:12]([C:14]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:21])([CH3:16])[CH3:15])#[N:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 83904-Methyl-3-nitroanilineHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Product 1

HCID 671255393-(1-Cyano-1-methylethyl)-N-(4-methyl-3-nitro-phenyl)benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a suspension of 3-(1-cyano-1-methylethyl)benzoic acid (9.87 g, 52.2 mmol) in toluene (150 mL) was added thionyl chloride (25.3 g, 213 mmol), and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was concentrated under reduced pressure to give 3-(1-cyano-1-methylethyl)benzoyl chloride as a colorless oil. To a solution of 4-methyl-3-nitroaniline (7.63 g, 50.2 mmol) in pyridine (150 mL) were added N,N-dimethylpyridine-4-amine (122 mg, 1.00 mmol) and 3-(1-cyano-1-methylethyl)benzoyl chloride, and the mixture was stirred at room temperature for 14 hr. To the reaction mixture was added 1N hydrochloric acid (200 mL), and the mixture was extracted with ethyl acetate (150 mL, 100 mL). The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (150 mL), and dried over anhydrous magnesium sulfate. After filtration through a silica gel pad, the filtrate was concentrated under reduced pressure to give 3-(1-cyano-1-methylethyl)-N-(4-methyl-3-nitrophenyl)benzamide as a yellow oil. The obtained compound was used for the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (150 mL, 100 mL)
  2. washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration through a silica gel pad
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-33cd2d0f2d974be2bea97603c6585d07
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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