Nitrogen → HCID 13914873, compound

HRID 1789589Notes

Reaction equation

HRID 1789589 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[C:20]1([CH2:26][C:27]([NH:29][NH2:30])=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N#N>C(O)CCC>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:27]([CH2:26][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:29][N:30]=[C:10]3[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 70301Benzeneacetic acid, hydrazideHCID 13914872HCID 13914872, compound

Product 1

HCID 13914873HCID 13914873, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A stirred mixture of 7-iodo-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione (3.78 g, 0.01 mol), phenylacetic acid hydrazide (4.5 g, 0.03 mol) and butanol (150 ml) was heated to reflux while N2 was bubbled through the mixture. After refluxing 17 hours the reaction mixture was concentrated under vacuum. The residue was combined with ice water and allowed to stir for a few minutes. The resulting suspension was filtered and the filtered material washed with CH2Cl2. The filtrate was separated into its respective layers and the aqueous layer washed with CH2Cl2. The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was triturated with EtOAc to yield 1.43 g (30.04%), mp 200°-201° of the subtitled intermediate. The analytical sample was recrystallized from EtOAc and had mp 201°-202°. The IR, NMR and mass spectra supported the proposed structure.

Workup

  1. temperaturewas heated
  2. customwas bubbled through the mixture
  3. temperatureAfter refluxing 17 hours the reaction mixture
  4. concentrationwas concentrated under vacuum
  5. filtrationThe resulting suspension was filtered
  6. washthe filtered material washed with CH2Cl2
  7. customThe filtrate was separated into its respective layers
  8. washthe aqueous layer washed with CH2Cl2
  9. washThe combined organic fractions were washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-86a8574d1bbd4dc79c000e9ef7eb8599
Source dataset
uspto-grants-1987_08
Patent number
US04689413

Reaction notes

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