Aniline → HCID 18963769, compound

HRID 2226881Notes

Reaction equation

HRID 2226881 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[C:7]([O:13][CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:17]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:12])=[C:7]([O:13][CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10587093HCID 10587093, compound

Product 1

HCID 18963769HCID 18963769, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-chloro-3-(1-methylethoxy)-2-benzofurancarboxylic acid (250 mg, 0.98 mmol) in 5 mL of dry tetrahydrofuran is added oxalyl chloride (0.10 mL, 1.18 mmol) followed by dimethylformamide (0.02 mL). The solution is stirred at room temperature for 1.75 hours, then aniline (0.54 mL, 5.88 mmol) is added. The solution is stirred at room temperature overnight then partitioned between ethyl acetate and 1N HCl . The organic layer is washed with saturated aqueous NaHCO3, followed by brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography eluting with 3:1 hexane:ethyl acetate to provide 5-chloro-3-(1-methylethoxy)-N-phenyl-2-benzofurancarboxamide, 86% yield; mp=147°-149° C.

Workup

  1. stirringThe solution is stirred at room temperature overnight
  2. customthen partitioned between ethyl acetate and 1N HCl
  3. washThe organic layer is washed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash chromatography
  8. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-05fb6085716b405bafd24de94befaa9c
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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