Triethylamine → 4-Cyano-N-(2-furan-2-ylphenyl)-3-methylbenzamide

HRID 558985Notes

Reaction equation

HRID 558985 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[CH3:12])#[N:2].S(Cl)(Cl)=O.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:18]2[O:17][CH:21]=[CH:20][CH:19]=2)=[O:9])=[CH:5][C:4]=1[CH3:12])#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 46853502-(Furan-2-yl)anilineHCID 102410994-Cyano-3-methylbenzoic acid

Product 1

HCID 574707854-Cyano-N-(2-furan-2-ylphenyl)-3-methylbenzamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyano-3-methylbenzoic acid from Example C (187 mg, 1.16 mmol) in toluene (10 ml) was added thionyl chloride (425 μl, 5.8 mmol). The mixture was heated at reflux for 2 h, cooled, evaporated in vacuo and azeotroped with toluene. The residue was taken up in CH2Cl2 (5.0 ml) and added to a solution of 2-furan-2-yl-phenylamine from Example 21A (185 mg, 1.16 mmol) and triethylamine (324 μl, 2.32 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 18 h, partitioned between water and chloroform and separated. The organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 80:20) to give a yellow solid; yellow solid 233 mg, 66%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. customevaporated in vacuo
  5. customazeotroped with toluene
  6. custompartitioned between water and chloroform
  7. customseparated
  8. customThe organic layers were dried
  9. customevaporated in vacuo
  10. customThe residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 80:20)
  11. customto give a yellow solid

Sources & evidence

ORD record
ord-1236b7ef6a3a430695c1014eb0b88a7d
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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