4-Aminobenzoic Acid → 4-(4-Methyl-2-benzoxazolyl)benzenamine

HRID 1401888ノート

反応式

HRID 1401888 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[C:17](O)=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19]>>[CH3:19][C:13]1[C:12]2[N:11]=[C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=3)[O:8][C:17]=2[CH:16]=[CH:15][CH:14]=1

参加物

3

反応物 2

HCID 9784-Aminobenzoic AcidHCID 30141382-Amino-m-cresol

生成物 1

HCID 50287054-(4-Methyl-2-benzoxazolyl)benzenamine

反応条件

温度
160 °C

実験手順

To a suspension of 4-amino-benzoic acid (2.0 g, 14.5 mmol) in PPA (˜85 g) was added 2-amino-m-cresol (1.8 g, 15.3 mmol). The reaction was heated to 160° C. for 14 h, then carefully quenched in aqueous sodium carbonate (˜50% saturated) at room temperature. Ethyl acetate was added, and the organic layer was washed with water and brine, and dried over sodium sulfate. The crude product was obtained was subsequently purified by flash column chromatography on silica gel eluting with ethyl acetate in hexanes to afford the desired product, 4-(4-methyl-benzooxazol-2-yl)-phenylamine as a light pink solid, 1.8 g (56%). LC-MS m/z=225 [C14H12N2O+H]+.

後処理

  1. customcarefully quenched in aqueous sodium carbonate (˜50% saturated) at room temperature
  2. additionEthyl acetate was added
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was obtained
  6. customwas subsequently purified by flash column chromatography on silica gel eluting with ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-5fef8a861f47485e81237a1d3bfa6666
出典データセット
uspto-grants-2014_12
特許番号
US08907103B2

反応ノート

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