Diazomethane → HCID 73165016, compound

HRID 1389436Notes

Reaction equation

HRID 1389436 reaction equation
[N+](=[CH2:3])=[N-].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]=[C:13]([C:15]([N+:18]([O-:20])=[O:19])=[N:16][OH:17])[CH2:12][N+:11]([O-:21])=[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:9]=2[CH:29]=1>CCOCC.C(Cl)Cl>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]=[C:13]([C:15]([N+:18]([O-:20])=[O:19])=[N:16][O:17][CH3:3])[CH2:12][N+:11]([O-:21])=[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:9]=2[CH:29]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 178526918HCID 178526918, compound

Product 1

HCID 73165016HCID 73165016, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of diazomethane in ether was added to a suspension of 3.8 g (0.01 mol) of 7-chloro-5-(2-fluorophenyl)-N-hydroxy-α-nitro-3H-1,4-benzodiazepine-2-methanimine 4-oxide in 200 ml of methylene chloride. The mixture was stirred for 1 hr at room temperature whereby a clear solution resulted. The excess diazomethane was destroyed by addition of acetic acid. The reaction mixture was washed with aqueous sodium bicarbonate solution, dried over sodium sulfate and evaporated. Crystallization of the residue from ether yielded yellow crystals. The analytical sample was recrystallized from ether, mp 207°-209°.

Workup

  1. customresulted
  2. customThe excess diazomethane was destroyed by addition of acetic acid
  3. washThe reaction mixture was washed with aqueous sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customCrystallization of the residue from ether yielded yellow crystals
  7. customThe analytical sample was recrystallized from ether, mp 207°-209°

Sources & evidence

ORD record
ord-9fb8c57727f941f4ac67d2688943eed9
Source dataset
uspto-grants-1981_01
Patent number
US04244868

Reaction notes

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