4-Methoxybenzoic Acid → N-(3-cyanophenyl)-4-methoxybenzamide

HRID 474478Notes

Reaction equation

HRID 474478 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH2:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[C:45]#[N:46]>CN(C=O)C.O>[C:45]([C:44]1[CH:43]=[C:42]([NH:41][C:7](=[O:9])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:49]=[CH:48][CH:47]=1)#[N:46]

Participants

8

Reactant 5

HCID 74784-Methoxybenzoic AcidHCID 79724-MethylmorpholineHCID 167023-AminobenzonitrileHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 904414N-(3-cyanophenyl)-4-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5.0 g (33 mmol) 4-methoxybenzoic acid were dissolved in 50 ml DMF. 12.8 g (66 mmol) EDCl, 9.2 g (66 mmol) HOBt and 14.8 ml (132 mmol) 4-methylmorpholine were added and the mixture was stirred for 15 min. Subsequently, 3.9 g (33 mmol) 3-aminobenzonitrile were added and the mixture was stirred for 48 h at room temperature and 6 h at 80° C. The reaction mixture was poured in 500 ml water and the precipitate was filtered, washed and dried.

Workup

  1. stirringthe mixture was stirred for 48 h at room temperature and 6 h at 80° C
  2. filtrationthe precipitate was filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-1bd2a35e59fc4454a584fd074e231b46
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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