Acetic Acid → Diisopropyl Ether

HRID 1764507Notes

Reaction equation

HRID 1764507 reaction equation
[NH2:1][C:2]1[CH:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[N:7]=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:4]=2[N:3]=1.O.[NH2:25]N.[CH3:27]O.[C:29]([OH:32])(=O)[CH3:30]>O>[CH:29]([O:32][CH:22]([CH3:21])[CH3:4])([CH3:30])[CH3:27].[Cl:23][C:20]1[CH:21]=[CH:22][C:4]2[N:3]=[C:2]([NH:1][NH2:25])[CH:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[N:7]=[C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]=2[CH:19]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 22768405HCID 22768405, compound

Product 2

HCID 7914Diisopropyl EtherHCID 22768404HCID 22768404, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 16 parts of 2-amino-7-chloro-3-isobutyl-5-phenyl-3H-1,4-benzodiazepine and 25 parts of 100% hydrazine hydrate in 400 parts by volume of methanol is added 6 parts of glacial acetic acid with stirring and ice-cooling. Then the whole mixture is stirred for 5 hours at room temperature. Water is added to the reaction mixture, followed by extraction with chloroform. The chloroform layer is washed with water, dried over sodium sulfate and the solvent is evaporated. Treatment of the residue with isopropyl ether yields 7-chloro-2-hydrazino-3-isobutyl-5-phenyl-3H-1,4-benzodiazepine as colorless crystals melting at 165° C to 168° C.

Workup

  1. temperatureice-cooling
  2. stirringThen the whole mixture is stirred for 5 hours at room temperature
  3. extractionfollowed by extraction with chloroform
  4. washThe chloroform layer is washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-677660bb98394819a2b32d0db3aa9da3
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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