Pyridine → HCID 53775232, 화합물

HRID 1604290노트

반응식

HRID 1604290 반응식
[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH:12]([CH2:14][CH2:15][CH2:16]O)[O:11][C:10]2=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.S(Cl)([Cl:27])=O>>[Cl:27][CH2:16][CH2:15][CH2:14][CH:12]1[O:11][C:10](=[O:18])[N:9]([N:8]=[CH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:13]1

참가 물질

4

반응물 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 54486637HCID 54486637, 화합물

생성물 1

HCID 53775232HCID 53775232, 화합물수율 95.9%

실험 절차

A mixture of 3-phenylmethyleneamino-5-(3-hydroxy) propyl-2-oxazolidinone (10.88 g, 0.0438 mole) CHCl3 (200 ml), and pyridine (4.25 ml, 4.16 g, 0.0526 mole, 1.2 eq.) is stirred at ambient temperature. Thionyl chloride (11.2 ml, 18.2 g, 0.1533 mole, 3.5 eq.) is added dropwise over 30-45 minutes while at ambient temperature (slight exotherm observed). After complete addition, the solution is heated to reflux. Reflux is maintained for 2 hours. After cooling, the solution is concentrated under reduced pressure to a solid residue, which is azeotroped with toluene (2×50 ml). The solid is dissolved in CH2Cl2 (250 ml), then washed with H2O (3×100 ml). The CH2Cl2 is dried over MgSO4, filtered, then concentrated under reduced pressure to give 5-(3-chloropropyl)-3-phenylmethyleneamino-2-oxazolidinone (11.2 g, 0.0420 mole) as a solid residue.

후처리

  1. additionAfter complete addition
  2. temperaturethe solution is heated to reflux
  3. temperatureReflux
  4. temperatureis maintained for 2 hours
  5. temperatureAfter cooling
  6. concentrationthe solution is concentrated under reduced pressure to a solid residue, which
  7. customis azeotroped with toluene (2×50 ml)
  8. dissolutionThe solid is dissolved in CH2Cl2 (250 ml)
  9. washwashed with H2O (3×100 ml)
  10. dry with materialThe CH2Cl2 is dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8cee5daf26264368ac471074f81ce3d0
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994354

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