Ammonia → 4-(Chloromethyl)-5-methyl-2-(naphthalen-2-yl)-1,3-oxazole

HRID 1373158노트

반응식

HRID 1373158 반응식
[CH3:1][C:2]1[N+:3]([O-])=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[O:5][C:6]=1[CH3:7].P(Cl)(Cl)([Cl:21])=O.N>C(Cl)(Cl)Cl>[Cl:21][CH2:1][C:2]1[N:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[O:5][C:6]=1[CH3:7]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 210742674,5-Dimethyl-2-naphthalen-2-yloxazole 3-oxide

생성물 1

HCID 121580734-(Chloromethyl)-5-methyl-2-(naphthalen-2-yl)-1,3-oxazole

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

40 g of 4,5-dimethyl-2-naphthalen-2-yloxazole 3-oxide are dissolved in 200 ml of chloroform, 16.7 ml of phosphorus oxychloride are added and the mixture is heated under reflux for 30 minutes. The reaction mixture is cooled to 0° C., a slightly alkaline pH is established using ammonia and the mixture is extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases are washed with water and dried over MgSO4 and the solvent is then removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=80:1=>5:1. This gives 10.6 g of 4-chloromethyl-5-methyl-2-naphthalen-2-yloxazole as a colorless solid. C15H12ClNO (257.72), MS(ESI): 258 (M+H+).

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. extractionthe mixture is extracted three times with in each case 500 ml of ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent is then removed under reduced pressure
  7. customThe residue is purified on silica gel using the mobile phase n-heptane

출처 및 근거

ORD 기록
ord-728b8dcc40a14d8e9ff4e598716ffde9
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160911B2

반응 노트

불러오는 중…