Potassium Carbonate → HCID 669673, compound

HRID 717351Notes

Reaction equation

HRID 717351 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22]>CCOCC>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:21](=[O:22])[C:20]1[CH:19]=[C:18]([O:17][CH3:16])[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=1)#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 729132-AminobenzonitrileHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

Product 1

HCID 669673HCID 669673, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a 1-L 3-necked round-bottom flask, was placed 2-aminobenzonitrile (20 g, 169.30 mmol, 1.00 equiv), ether (500 mL) and potassium carbonate (75 g, 542.65 mmol, 3.21 equiv). This was followed by the addition of 3,4,5-trimethoxybenzoyl chloride (40 g, 173.43 mmol, 1.02 equiv) in several batches at reflux. The mixture was stirred overnight at reflux. The resulting solution was cooled to room temperature. The reaction was then quenched by the addition of 500 mL of water. The solids were collected by filtration. This resulted in 22 g (42%) of N-(2-cyanophenyl)-3,4,5-trimethoxybenzamide as a yellow solid. MS (ESI) m/z 313 ([M+H]+).

Workup

  1. customInto a 1-L 3-necked round-bottom flask, was placed
  2. temperatureat reflux
  3. temperatureat reflux
  4. customThe reaction was then quenched by the addition of 500 mL of water
  5. filtrationThe solids were collected by filtration
  6. customThis resulted in 22 g (42%) of N-(2-cyanophenyl)-3,4,5-trimethoxybenzamide as a yellow solid

Sources & evidence

ORD record
ord-55712704b0744abc9ff2ae0271154d6a
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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