1-Amino-2-propanol → Oxazolam

HRID 328480

反応式

HRID 328480 の反応式
Br[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])=[O:4].C1(C)C(C)=CC=CC=1.[NH2:29][CH2:30][CH:31](O)[CH3:32].C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C.CCCCCC>[Cl:20][C:17]1[CH:18]=[CH:19][C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:29]3[CH2:30][CH:31]([CH3:32])[O:9][C:8]3([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]=2[CH:16]=1

参加物

8

反応物 4

HCID 41-Amino-2-propanolHCID 7237O-XyleneHCID 8471TriethylamineHCID 122906N-(2-benzoyl-4-chlorophenyl)-2-bromoacetamide

生成物 1

HCID 4617Oxazolam

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 67 g. (0.19 mole) of 2-(2-bromoacetamido)-5-chloro-benzophenone, 500 ml. of xylene, 15.7 g. (0.21 mole) of 1-amino-2-propanol and 25 ml. of triethylamine was stirred at reflux for 20 hours. The reaction mixture was concentrated in vacuo to a residue which was partitioned between methylene chloride and water. The organic layer was washed with water, dried and concentrated to an oil which was crystallized from ethyl acetate to give 18.3 g. of a colorless solid, m.p. 181°-184°. Thin layer chromatography on Eastman alumina plates with an eluant of 3 parts of hexane and 2 parts of ethyl acetate revealed the prsence of two compounds. The product was dissolved in chloroform and chromatographed over Woelm neutral alumina I. A mixture concentrated in the above-titled product (the faster of the two compounds) was collected in 30% ethyl acetate-70% hexane. Recrystallizations from methylene chloride gave colorless prisms, m.p. 188°-189°.

後処理

  1. temperatureat reflux for 20 hours
  2. concentrationThe reaction mixture was concentrated in vacuo to a residue which
  3. customwas partitioned between methylene chloride and water
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated to an oil which
  7. customwas crystallized from ethyl acetate
  8. customto give 18.3 g
  9. customchromatographed over Woelm neutral alumina I
  10. concentrationA mixture concentrated in the above-titled product (the faster of the two compounds)
  11. customwas collected in 30% ethyl acetate-70% hexane
  12. customRecrystallizations from methylene chloride
  13. customgave colorless prisms, m.p. 188°-189°

出典と根拠

ORDレコード
ord-9c9fe9dbfb5f4c36a0788a8f20953a88
出典データセット
uspto-grants-1977_04
特許番号
US04017531

関連ノート

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