Benzenamine, 3-(4-nitrophenoxy)- → 3-(1-cyanocyclopropyl)-N-[3-(4-nitrophenoxy)phenyl]benzamide

HRID 2190397Notes

Reaction equation

HRID 2190397 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]1([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[CH2:22][CH2:21]1)#[N:19].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:18]([C:20]1([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26]([NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[C:9]([O:8][C:7]3[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH:10]=2)=[O:27])[CH2:21][CH2:22]1)#[N:19]

Participants

6

Reactant 3

HCID 211166Benzenamine, 3-(4-nitrophenoxy)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574410393-(1-Cyanocyclopropyl)benzoic acid

Product 1

HCID 673112323-(1-cyanocyclopropyl)-N-[3-(4-nitrophenoxy)phenyl]benzamideYield 91.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using 3-(4-nitrophenoxy)aniline (3.21 g, 13.9 mmol) produced in Example A12(i), 3-(1-cyanocyclopropyl)benzoic acid (2.70 g, 14.4 mmol) produced in Example A1(iii), pyridine (100 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.20 g, 16.7 mmol) and N,N-dimethylpyridine-4-amine (122 mg, 997 μmol) as starting materials, and in the same manner as in Example A12(ii), the title compound (5.1 g, 91%) was obtained as a yellow amorphous substance.

Sources & evidence

ORD record
ord-74ddbc193a8940c9858404f74f3c68c0
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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