Hydrochloric Acid → 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)one

HRID 247269

反応式

HRID 247269 の反応式
[OH-].[Na+].[CH3:3][N:4]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](N)=[O:13])[CH2:5]1.[ClH:19]>O>[Cl:19][CH2:8][CH2:7][CH:6]1[CH2:5][N:4]([CH3:3])[C:12](=[O:13])[C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[O:9]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 137262832-[(1-Methyl-3-pyrrolidinyl)oxy]benzamide

生成物 1

HCID 137262932-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 54 g (1.35 mole) of sodium hydroxide in 800 ml of water was added 148 g (0.67 mole) of 2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide and the mixture brought to reflux for 18 hr. The pH was adjusted to 7 with hydrochloric acid and the solution filtered and concentrated. The residue was boiled with 400 ml of isopropanol and filtered. The filtrate was concentrated and the residue (which crystallized) was refluxed with 300 ml of thionyl chloride for 0.5 hr. and concentrated in vacuo. The residue was dissolved in 300 ml of chloroform and the solvent boiled off in vacuo. The residue was redissolved in chloroform, 150 ml of triethyl amine added and the mixture refluxed 1 hr. The solution was concentrated in vacuo and the residue partitioned between 400 ml of ethyl acetate, 400 ml of isopropyl ether and 500 ml of dilute hydrochloric acid. The organic layer was washed twice with water and once with dilute sodium hydroxide, dried with sodium sulfate and concentrated. The residue was crystallized from isopropanol-water. Yield of product was 75 g (47%), m.p. 97°-107° C.

後処理

  1. temperatureto reflux for 18 hr
  2. filtrationthe solution filtered
  3. concentrationconcentrated
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue (which crystallized)
  7. temperaturewas refluxed with 300 ml of thionyl chloride for 0.5 hr
  8. concentrationand concentrated in vacuo
  9. dissolutionThe residue was dissolved in 300 ml of chloroform
  10. dissolutionThe residue was redissolved in chloroform
  11. addition150 ml of triethyl amine added
  12. temperaturethe mixture refluxed 1 hr
  13. concentrationThe solution was concentrated in vacuo
  14. customthe residue partitioned between 400 ml of ethyl acetate, 400 ml of isopropyl ether and 500 ml of dilute hydrochloric acid
  15. washThe organic layer was washed twice with water and once with dilute sodium hydroxide
  16. dry with materialdried with sodium sulfate
  17. concentrationconcentrated
  18. customThe residue was crystallized from isopropanol-water

出典と根拠

ORDレコード
ord-8c698d90badb4510abfcbfbb3f21cac4
出典データセット
uspto-grants-1987_11
特許番号
US04705853

関連ノート

読み込み中…