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

HRID 249824노트

반응식

HRID 249824 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

반응 조건

온도
95 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2e994a9771c5421094e686623bff71a1
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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