Hydrochloric Acid → 9-chloro-2-methyl-7-phenyl-5H[1,2,4]triazolo-[5,1-a] [2,4]benzodiazepine

HRID 616908ノート

反応式

HRID 616908 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1=[N:11][C:12]([CH3:14])=[N:13][N:6]1[C:5]2([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:15].[CH2:22]1N2CN3CN(C2)CN1C3.Cl>COCCOC>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[C:7]3=[N:11][C:12]([CH3:14])=[N:13][N:6]3[CH2:22][N:15]=[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 4101Hexamethylenetetramine2 回HCID 124680237-Chloro-2-methyl-5-phenyl-5H-[1,2,4]triazolo[5,1-a]isoindol-5-amine

生成物 1

HCID 124680259-chloro-2-methyl-7-phenyl-5H[1,2,4]triazolo-[5,1-a] [2,4]benzodiazepine収率 40.5%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a stirring solution of 3.1 g (10.4 mmol) of 7-chloro-2-methyl-5-phenyl-5H-[1,2,4]triazolo[5,1-a]-isoindol-5-amine and 3.1 g (22 mmol) of hexamethylenetetramine (hexamine) in 75 ml of DME is added 1.5 ml of 4 N HCl (dioxane). A precipitate forms immediately and the two phase mixture is refluxed. After 5 hours another 1.0 g of hexamine is added and reflux is continued overnight. An additional 1.5 ml of the HCl solution is added after 12 hours and again after an additional 24 hours. After another 24 hours, thin layer chromatography (TLC) shows the disappearance of starting material. The mixture is filtered and the solvent is removed from the filtrate under vacuum. The residue is taken up in CHCl3 and applied to a 5×10 cm silica gel column (Baker 60-200 mesh). The column is eluted with CHC13 until all of the high Rf material (followed by TLC) is recovered. The solvent is removed in vacuo and the residue recrystallized from 20 ml of acetonitrile to yield 1.3 g of pure product: m.p. 150.5°-152° [concentration of the mother liquor gives an additional 0.2 g for a total yield of 1.5 g (46.6%)].

後処理

  1. temperatureA precipitate forms immediately and the two phase mixture is refluxed
  2. temperaturereflux
  3. waitAfter another 24 hours
  4. filtrationThe mixture is filtered
  5. customthe solvent is removed from the filtrate under vacuum
  6. washThe column is eluted with CHC13 until all of the high Rf material (followed by TLC)
  7. customis recovered
  8. customThe solvent is removed in vacuo
  9. customthe residue recrystallized from 20 ml of acetonitrile

出典と根拠

ORDレコード
ord-b362991737ce4fbcbb7df3a5a34cb890
出典データセット
uspto-grants-1978_02
特許番号
US04076823

反応ノート

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