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

HRID 1373158ノート

反応式

HRID 1373158 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-728b8dcc40a14d8e9ff4e598716ffde9
出典データセット
uspto-grants-2007_01
特許番号
US07160911B2

反応ノート

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