Phosphorus pentachloride → 2-Chloro-5-phenylbenzoxazole

HRID 1815755

반응식

HRID 1815755 반응식
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13](=S)[NH:12][C:11]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:18]>P(Cl)(Cl)(Cl)=O>[Cl:18][C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:16][C:11]=2[N:12]=1

참가 물질

4

반응물 2

HCID 24819Phosphorus pentachlorideHCID 30326635-Phenyl-2(3H)-benzoxazolethione

생성물 1

HCID 141698182-Chloro-5-phenylbenzoxazole수율 640.1%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

5-Phenyl-3H-benzooxazole-2-thione (227 mg, 1.0 mmol) was dissolved in phosphorus oxychloride (1.6 mL). Phosphorus pentachloride (208 mg, 1.0 mmol) was added and the mixture was placed in an oil bath at 100° C. for 3 h. The mixture was allowed to cool to RT and concentrated. The crude residue was concentrated from CH2Cl2 (3×). The crude reaction product was triturated with hexanes (40 mL), and the resulting solids were collected by filtration. The solids were washed with hexanes (20 mL×3) and dried to afford 1.47 g (73%) of the title compound: 1H NMR (CDCl3, 400 MHz) δ 7.86 (d, 1H, J=1.3 Hz), 7.60-7.56 (m, 3H), 7.55-7.52 (m, 1H), 7.49-7.44 (m, 2H), 7.40-7.36 (m, 1H); 13C NMR (CDCl3, 100 MHz) δ 151.6, 151.4, 141.9, 140.7, 139.3, 129.2, 127.8, 127.7, 125.2, 118.4, 110.7; MS (Cl) m/z 230.1 (M+1); HPLC retention time=5.41 min.

후처리

  1. concentrationconcentrated
  2. concentrationThe crude residue was concentrated from CH2Cl2 (3×)
  3. customThe crude reaction product
  4. customwas triturated with hexanes (40 mL)
  5. filtrationthe resulting solids were collected by filtration
  6. washThe solids were washed with hexanes (20 mL×3)
  7. customdried

출처 및 근거

ORD 기록
ord-8bc6c6de71bc402f866dccdc05727d65
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881734B2

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