Phosphorus oxychloride → 2-(Chloromethyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole

HRID 334512

반응식

HRID 334512 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][NH:9][C:10](=[O:13])[CH2:11][Cl:12])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:12][CH2:11][C:10]1[O:13][C:6]([C:5]2[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:8][N:9]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 5212924-chloro-N'-(2-chloroacetyl)benzohydrazide

생성물 1

HCID 12682462-(Chloromethyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole수율 82%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 4-chlorobenzohydrazide 5 (1 g, 5.86 mmol) and K2CO3 (0.97 g, 7.03 mmol) in acetonitrile (30 mL) was added 2-chloroacetyl chloride (0.68 g, 6.08 mmol) dropwise at ambient temperature. The resulting mixture was stirred at ambient temperature for 16 hours. The solid was collected, washed with H2O and ether, and dried to afford 4-chloro-N′-(2-chloroacetyl)benzohydrazide 6 (1.2 g, 82%) which was used for the next step without further purification. A mixture of 4-chloro-N′-(2-chloroacetyl)benzohydrazide 6 (0.6 g, 2.43 mmol) and phosphorous oxychloride (0.37 g, 2.43 mmol) in acetonitrile (20 mL) was stirred under reflux for 16 hours and concentrated. The residue was subjected to flush column chromatography eluting with 10-25% acetone/hexanes to give compound 7 (0.45 g). Yield: 82%.

후처리

  1. customwas used for the next step without further purification
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated
  4. customto flush column chromatography
  5. washeluting with 10-25% acetone/hexanes

출처 및 근거

ORD 기록
ord-403a30879bc547fca00d9fe10fd8f003
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883827B2

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