Chloroacetonitrile → HCID 14279665、化合物

HRID 1381817ノート

反応式

HRID 1381817 の反応式
[F:1][C:2]1[C:12]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:31][C:32]#[N:33]>C(#N)C>[F:1][C:2]1[C:12]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])=[CH:11][C:5]2[N:6]([CH2:31][C:32]#[N:33])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 137721852-(7-Fluoro-3-oxo-4H-1,4-benzoxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione

生成物 1

HCID 14279665HCID 14279665、化合物収率 37.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
5 °C

実験手順

A suspension of 2-[7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (2 g) and potassium carbonate (1.05 g) in acetonitrile (30 ml) is refluxed for 30 minutes. The resulting solution is cooled to a temperature of 5° C. To the solution is added dropwise chloroacetonitrile (0.72 g), and thereafter the solution is refluxed for 3 hours. The solvent is distilled off, and the residue is admixed with water and subjected to an extraction operation with the aid of dichloromethane. The dichloromethane layer is separated off, washed with water, and dried over sodium sulfate. The solution is concentrated to precipitate a crystalline product, which is then recrystallized in a solvent consisting of acetonitrile and water. As an end product, 2-[7-fluoro-4-cyanomethyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.84 g) is obtained. mp. 216°-220° C.

後処理

  1. temperatureis refluxed for 30 minutes
  2. temperaturethe solution is refluxed for 3 hours
  3. distillationThe solvent is distilled off
  4. customThe dichloromethane layer is separated off
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe solution is concentrated
  8. customto precipitate a crystalline product, which
  9. customis then recrystallized in a solvent

出典と根拠

ORDレコード
ord-6932387b295e4072bd3e5db202965271
出典データセット
uspto-grants-1989_02
特許番号
US04804394

反応ノート

読み込み中…