Sodium Iodide → HCID 22405074, compound

HRID 441261Notes

Reaction equation

HRID 441261 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:36]=[CH:35][CH:34]=[CH:33][C:9]=2[C:10]([NH:12][C:13]2[CH:32]=[CH:31][C:16]([C:17]([N:19]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[NH:23][C:22](=[S:30])[CH2:21][CH2:20]3)=[O:18])=[CH:15][CH:14]=2)=[O:11])=[CH:4][CH:3]=1.Cl.[CH3:38][N:39]([CH3:44])[CH2:40][CH2:41][CH2:42]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:38][N:39]([CH3:44])[CH2:40][CH2:41][CH2:42][S:30][C:22]1[CH2:21][CH2:20][N:19]([C:17](=[O:18])[C:16]2[CH:31]=[CH:32][C:13]([NH:12][C:10](=[O:11])[C:9]3[CH:33]=[CH:34][CH:35]=[CH:36][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:14][CH:15]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 57261969HCID 57261969, compound

Product 1

HCID 22405074HCID 22405074, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(4-[2-(4-methylphenyl)benzoylamino]-benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepine-2(2H)thione (460 mg), 3-dimethylaminopropyl chloride hydrochloride (740 mg), potassium carbonate (1.29 g) and sodium iodide (catalytic amount) in acetone (40 ml) was stirred for 19 hours at 60° C. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography (SiO2 30 g, 5% methanol in chloroform) to give 2-[3-(dimethylamino)propylthio]-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-4,5-dihydro-3H-1,5benzodiazepine (200 mg).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography (SiO2 30 g, 5% methanol in chloroform)

Sources & evidence

ORD record
ord-e9ea76ba2a1f4c21be086e6109c5a73b
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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