Triphenylphosphine → 2-ethoxy-7-nitro-5-phenyl-3H-1,4-benzodiazepine

HRID 867061Notes

Reaction equation

HRID 867061 reaction equation
[N:1]([CH2:4][C:5](=[N:9][C:10]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)[O:6][CH2:7][CH3:8])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH2:7]([O:6][C:5]1[CH2:4][N:1]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:10]=2[N:9]=1)[CH3:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 203172632-(2-Azido-1-ethoxyethylideneamino)-5-nitrobenzophenone

Product 1

HCID 203172642-ethoxy-7-nitro-5-phenyl-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.5 parts of 2-(2-azido-1-ethoxyethylideneamino)-5-nitrobenzophenone produced in Step (2) in 30 parts by volume of benzene is added with stirring 1.78 parts of triphenylphosphine. The mixture is stirred for further 1.5 hours and the solvent is removed by distillation. The residue is extracted with a mixture of n-hexane and acetone (7:3), and the soluble fraction is purified by means of chromatography employing Silica Gel, whereupon 2-ethoxy-7-nitro-5-phenyl-3H-1,4-benzodiazepine is obtained as pale yellow crystals. Recrystallization from ether-n-hexane gives pale yellow prisms melting at 143°-145° C.

Workup

  1. customthe solvent is removed by distillation
  2. extractionThe residue is extracted with a mixture of n-hexane and acetone (7:3)
  3. customthe soluble fraction is purified by means of chromatography

Sources & evidence

ORD record
ord-e605eaf53e8a4d72bd3be540b5d972d5
Source dataset
uspto-grants-1978_07
Patent number
US04102881

Reaction notes

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