Methanol → 3-[(3-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester

HRID 1524263Notes

Reaction equation

HRID 1524263 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](O)=[O:22])[CH:14]=1.P(Cl)(Cl)(Cl)=O.CO>N1C=CC=CC=1.O>[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](=[O:22])[NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=2)[CH:14]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 167023-AminobenzonitrileHCID 24813Phosphorus oxychlorideHCID 13816150[3-(Methoxycarbonyl)phenoxy]acetic acid

Product 1

HCID 81732703-[(3-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl esterYield 102.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Cool a solution of 3-aminobenzonitrile (0.35 g, 2.96 mmol) in pyridine (6 mL), to 0° C., and add 3-carboxymethoxy-benzoic acid methyl ester (0.75 g, 3.57 mmol) followed by phosphorous oxychloride (0.34 mL, 3.6 mmol). Warm the mixture to room temperature and stir for 15 hours. Dilute the mixture with water causing a material to oil out of solution. Add MeOH and stir the mixture vigorously causing a solid to slowly form. Collect the solid by filtration, wash with water and dry on the filter pad to provide 0.940 g of 3-[(3-cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester.

Workup

  1. customto slowly form
  2. customCollect the solid
  3. filtrationby filtration
  4. washwash with water
  5. customdry on the filter pad

Sources & evidence

ORD record
ord-40a8e0df70f446bbbfc3bc380c447f77
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

Loading…