Diazomethane → HCID 54384993, compound

HRID 903095Notes

Reaction equation

HRID 903095 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]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C:9]=2[CH:28]=1>CCOCC.O1CCCC1>[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]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C:9]=2[CH:28]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 136335629HCID 136335629, compound

Product 1

HCID 54384993HCID 54384993, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of diazomethane in ether was added to a suspension of 6 g (0.0163 mole) of 7-chloro-5-(2-fluorophenyl)-N-hydroxy-α-nitro-3H-1,4-benzodiazepine-2-methanimine in 100 ml of tetrahydrofuran. After sitting at room temperature for 1 hr the excess diazomethane was destroyed by addition of glacial acetic acid. The solvent was evaporated under reduced pressure and the residue was passed over 100 g of silica gel using methylene chloride. Crystallization from ether/hexane gave light yellow crystals with mp 130°-133° C.

Workup

  1. customthe excess diazomethane was destroyed by addition of glacial acetic acid
  2. customThe solvent was evaporated under reduced pressure
  3. customCrystallization from ether/hexane
  4. customgave light yellow crystals with mp 130°-133° C.

Sources & evidence

ORD record
ord-84ac922da2bd46878d7f8f9a81a7d560
Source dataset
uspto-grants-1980_10
Patent number
US04226768

Reaction notes

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