Tetrahydrofuran → HCID 178514336, compound

HRID 441972Notes

Reaction equation

HRID 441972 reaction equation
[NH2:1]N.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]=[C:12]([NH:14]CN=O)[CH2:11][N+:10]([O-:18])=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8]=2[CH:25]=1.O1CCCC1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]=[C:12]([NH:14][NH2:1])[CH2:11][N+:10]([O-:18])=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8]=2[CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 178526373HCID 178526373, compound

Product 1

HCID 178514336HCID 178514336, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 ml. of anhydrous hydrazine was added to a solution of 10 g. of 7-chloro-2-(N-nitrosomethylamino)-5-phenyl-3H-1,4-benzodiazepine 4-oxide in 100 ml. of tetrahydrofuran and 50 ml. of methanol. After sitting at room temperature for 1 hour, the reaction mixture was evaporated under reduced pressure. The crystalline residue was partitioned between methylene chloride and water. The methylene chloride solution was dried and evaporated. Crystallization from methylene chloride/ether yielded 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine 4-oxide with a melting point of 290°-292° dec.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customThe crystalline residue was partitioned between methylene chloride and water
  3. dry with materialThe methylene chloride solution was dried
  4. customevaporated
  5. customCrystallization from methylene chloride/ether

Sources & evidence

ORD record
ord-60100b1332fc4c6eb001c6d254ae8b82
Source dataset
uspto-grants-1977_08
Patent number
US04044016

Reaction notes

Loading…