Aniline → 2-(2,6-difluorophenyl)-5-ethoxy-N-phenyloxazole-4-carboxamide

HRID 389744Notes

Reaction equation

HRID 389744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([O:17][CH2:18][CH3:19])=[C:12]([C:14]([OH:16])=O)[N:13]=1.O.O[C:22]1[C:30]2N=N[NH:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.N=C=N.NC1C=CC=CC=1>C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[O:10][C:11]([O:17][CH2:18][CH3:19])=[C:12]([C:14]([NH:27][C:26]2[CH:30]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:16])[N:13]=1

Participants

6

Reactant 4

HCID 6115Aniline2×HCID 160435CarbodiimideHCID 595875182-(2,6-Difluorophenyl)-5-ethoxyoxazole-4-carboxylic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 595874842-(2,6-difluorophenyl)-5-ethoxy-N-phenyloxazole-4-carboxamideYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,6-difluorophenyl)-5-ethoxyoxazole-4-carboxylic acid (0.10 g, 0.37 mmol) and hydroxybenzotriazole monohydrate (0.06 g, 0.39 mmol) in DCM (4 mL) was added PS-carbodiimide resin (0.36 g, 0.45 mmol, 1.25 mmol/g) followed by aniline (39 uL, 0.43 mmol). The resulting mixture was stirred at room temperature for 4 hours when a further portion of aniline (7 uL, 0.08 mmol) was added and the reaction stirred at room temperature overnight. The mixture was filtered through a silica-carbonate cartridge, followed by a MP-TsOH resin cartridge which was rinsed with DCM and MeOH to afford 2-(2,6-difluorophenyl)-5-ethoxy-N-phenyloxazole-4-carboxamide (0.13 g) which was used without further purification. LCMS (1) Rt: 2.30; m/z (ES+) 345.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered through a silica-carbonate cartridge
  3. washwas rinsed with DCM and MeOH

Sources & evidence

ORD record
ord-5d3cf8a877ac48a6b14025c65f5bc748
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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