Tetrahydrofuran → 1-(2,4-Difluorophenyl)-2-(2-iminooxazol-3(2H)-yl)ethanone hydrobromide

HRID 1930036ノート

反応式

HRID 1930036 の反応式
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=[O:4].[O:13]1[CH:17]=[CH:16][N:15]=[C:14]1[NH2:18].C1COCC1>C(#N)C>[BrH:1].[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:15]1[CH:16]=[CH:17][O:13][C:14]1=[NH:18]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 5585212-AminooxazoleHCID 27741852-Bromo-2',4'-difluoroacetophenone

生成物 1

HCID 685187241-(2,4-Difluorophenyl)-2-(2-iminooxazol-3(2H)-yl)ethanone hydrobromide収率 61%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A round bottom flask was charged with 2-bromo-1-(2,4,-difluorophenyl)ethanone (74.8 g, 318 mmol), oxazol-2-amine (GL Synthesis, 22.3 g, 265 mmol), THF (400 mL), and ACN (660 mL). The resulting mixture was stirred at ambient temperature for about 20 h. The resulting suspension was filtered and the solids were washed with Et2O (150 mL) and dried under reduced pressure to give 1-(2,4-difluorophenyl)-2-(2-iminooxazol-3(2H)-yl)ethanone hydrobromide (51.4 g, 61%). A portion of this material (19.8 g, 62.0 mmol) was added in 3 g portions over about 2 h to a flask charged with polyphosphoric acid (124.4 g) at about 80° C. The thick solution was mixed at about 80-90° C. for about 22 h. The reaction mixture was slowly transferred to a mixture of water (150 mL) and 30% aqueous NaOH (150 mL) at about 5-10° C. The pH of the resulting slurry was adjusted to about 5.4 by addition of 30% aqueous NaOH and the product was isolated by filtration. The wet cake was rinsed with warm water (3×150 mL) and dried under vacuum to give the title compound (9.5 g, 69%). MS m/z 221.1 (M+H)+ FIA(APCI)

後処理

  1. filtrationThe resulting suspension was filtered
  2. washthe solids were washed with Et2O (150 mL)
  3. customdried under reduced pressure

出典と根拠

ORDレコード
ord-b3baef47dc5d4a9886bf6b7435a255c2
出典データセット
uspto-grants-2012_05
特許番号
US08188083B2

反応ノート

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