Acetohydrazide → HCID 20350618, compound

HRID 972092Notes

Reaction equation

HRID 972092 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10](SC)[N:9]([CH3:14])[N:8]=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[CH:21]=1.[C:22]([NH:25][NH2:26])(=O)[CH3:23]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:22]([CH3:23])=[N:25][N:26]=[C:10]3[N:9]([CH3:14])[N:8]=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 6287943H-1,3,4-Benzotriazepine, 7-chloro-3-methyl-2-(methylthio)-5-phenyl-

Product 1

HCID 20350618HCID 20350618, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 7.25 grams (23.0 m moles) of 7-chloro-3-methyl-(methylthio)-5-phenyl-3H-1,3,4-benzotriazepine (Example 27), 4.8 grams (65 moles) of acethydrazide, and 100 ml of n-butanol was stirred and refluxed under nitrogen for about 17 hours. The solvent was removed in vacuo on a rotary evaporator. The residue was dissolved in methylene chloride. The resulting solution was washed with water, dried with magnesium sulfate, and concentrated in vacuo. The residue was dissolved in a minimum amount of warm carbon tetrachloride. The solution was cooled and seeded with product. The precipitate was collected, washed with cold carbon tetrachloride, and air dried to yield the title compound as a yellow solid. The melting point was found to be 225.5°-227.5° C. The structure was confirmed by elemental analysis.

Workup

  1. temperaturerefluxed under nitrogen for about 17 hours
  2. customThe solvent was removed in vacuo on a rotary evaporator
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washThe resulting solution was washed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in a minimum amount of warm carbon tetrachloride
  8. temperatureThe solution was cooled
  9. customThe precipitate was collected
  10. washwashed with cold carbon tetrachloride, and air
  11. customdried

Sources & evidence

ORD record
ord-cbc504c41adb446d9f1b10e64dd1a9f5
Source dataset
uspto-grants-1979_07
Patent number
US04163104

Reaction notes

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