Hydrochloric Acid → 1-(3-Methylbutyl)-5-phenyl-1H-1,5-benzodiazepine-2,3,4-(5H)-trione-3-(phenylhydrazone)

HRID 1684514Notes

Reaction equation

HRID 1684514 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][CH2:4][NH:5][C:6]1[C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:9]=[CH:10][CH:11]=1.[C:20]1([NH:26][N:27]=[C:28]([C:32](Cl)=[O:33])[C:29](Cl)=[O:30])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C1COCC1>[C:20]1([NH:26][N:27]=[C:28]2[C:32](=[O:33])[N:5]([CH2:4][CH2:3][CH:2]([CH3:19])[CH3:1])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:29]2=[O:30])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 105144812-(Phenylhydrazono)-propanedioyl dichlorideHCID 57246343N1-(3-Methylbutyl)-N2-phenyl-1,2-benzenediamine

Product 1

HCID 544011821-(3-Methylbutyl)-5-phenyl-1H-1,5-benzodiazepine-2,3,4-(5H)-trione-3-(phenylhydrazone)Yield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

Solutions of N1 -(3-Methylbutyl)-N2 -phenyl-1,2-benzenediamine (12.45 g) in dry THF (100 ml) and (phenylhydrazono)propandioyl dichloride (12.0 g) in dry THF (100 ml) were added dropwise concurrently to a flask of dry THF (100 ml) cooled in an ice-methanol bath under nitrogen. After 30 min more diacid chloride (1.0 g) in dry THF (30 ml) was added and the mixture was allowed to warm to 23°. After 24 h the mixture was poured into dilute HCl and extracted with EA. The combined extracts were washed with dilute sodium carbonate and saturated brine then dried and evaporated. The residue was chromatographed on TEA deactivated silica with EA as eluent to give the title compound (20.2 g) as a yellow solid, m.p. 143°

Workup

  1. temperaturecooled in an ice-methanol bath under nitrogen
  2. temperatureto warm to 23°
  3. extractionextracted with EA
  4. washThe combined extracts were washed with dilute sodium carbonate and saturated brine
  5. customthen dried
  6. customevaporated
  7. customThe residue was chromatographed on TEA

Sources & evidence

ORD record
ord-4fba71e7a3474cada333306999f921aa
Source dataset
uspto-grants-1997_06
Patent number
US05641775

Reaction notes

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