Methanol → 3-(1-cyano-1-methylethyl)-N-[3-(4-nitrophenoxy)phenyl]benzamide

HRID 2190392Notes

Reaction equation

HRID 2190392 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:18]([C:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](O)=[O:27])([CH3:22])[CH3:21])#[N:19].Cl.C(N=C=NCCCN(C)C)C.CO>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:18]([C:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([O:8][C:7]2[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:10]=1)=[O:27])([CH3:22])[CH3:21])#[N:19]

Participants

7

Reactant 4

HCID 887MethanolHCID 211166Benzenamine, 3-(4-nitrophenoxy)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 571495383-(2-Cyanopropan-2-yl)benzoic acid

Product 1

HCID 573868263-(1-cyano-1-methylethyl)-N-[3-(4-nitrophenoxy)phenyl]benzamideYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 3-(4-nitrophenoxy)aniline (4.69 g, 20.4 mmol) and 3-(1-cyano-1-methylethyl)benzoic acid (3.98 g, 21.0 mmol) produced in Example A7(ii) in pyridine (100 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.69 g, 24.5 mmol) and N,N-dimethylpyridine-4-amine (151 mg, 1.24 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added methanol (50 mL) and the mixture was further stirred at the same temperature for 30 min. The solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), washed with dilute hydrochloric acid (150 mL×2) and saturated aqueous sodium hydrogencarbonate solution (150 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (8.10 g, 99%) as a yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.

Workup

  1. stirringthe mixture was further stirred at the same temperature for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate (200 mL)
  4. washwashed with dilute hydrochloric acid (150 mL×2) and saturated aqueous sodium hydrogencarbonate solution (150 mL)
  5. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cbe1fa2ddb2b4b9b84126ca98a781ac8
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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