Phosphorus pentachloride → Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

HRID 249824

反応式

HRID 249824 の反応式
S=[C:2]1[NH:6][C:5]2=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=[C:4]2[O:3]1.P(Cl)(Cl)(Cl)(Cl)[Cl:16]>P(Cl)(Cl)(Cl)=O>[Cl:16][C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1

参加物

4

反応物 2

HCID 24819Phosphorus pentachlorideHCID 22272869Methyl 2-thioxo-2,3-dihydrobenzoxazole-4-carboxylate

生成物 1

HCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate収率 100.3%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
95 °C

実験手順

A mixture of the thione from Step B (0.65 g, 3.11 mmol) and phosphorus pentachloride (0.65 g, 3.11 mmol) in phosphorus oxychloride (6 mL) was heated to 95° C. for 2.5 h. After cooling to room temperature, the reaction mixture was concentrated and dried on vacuum to give methyl 2-chlorobenzoxazole-4-carboxylate (0.66 g, quantitative) as a brown solid: 1H NMR (300 MHz, CDCl3) δ 8.05 (dd, J 8.1, 1.2 Hz, 1H), 7.72 (dd, J 8.1, 1.2 Hz, 1H), 7.45 (t, J=8.1 Hz, 1H), 4.04 (s, 3H); MS (ESI+) m/z 212 (M+H).

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customdried on vacuum

出典と根拠

ORDレコード
ord-2e994a9771c5421094e686623bff71a1
出典データセット
uspto-grants-2011_01
特許番号
US07863271B2

関連ノート

読み込み中…