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

HRID 578717Notes

Reaction equation

HRID 578717 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.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH2:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[C:44]#[N:45]>CN(C=O)C.O>[C:44]([C:43]1[CH:42]=[C:41]([NH:40][C:7](=[O:9])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:48]=[CH:47][CH:46]=1)#[N:45]

Participants

8

Reactant 5

HCID 74784-Methoxybenzoic AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 167023-AminobenzonitrileHCID 757711-Hydroxybenzotriazole

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) EDCI, 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-57bfeb9d643b49f2a2ebc6786bfc27a4
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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