Diazomethane → HCID 73165016, compound

HRID 128189Notes

Reaction equation

HRID 128189 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-beeb806c4bd446b7bce449102156f0ac
Source dataset
uspto-grants-1981_03
Patent number
US04259241

Reaction notes

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