Diisopropylethylamine → HCID 136411679, compound

HRID 983806Notes

Reaction equation

HRID 983806 reaction equation
[Br:1][C:2]1[C:3]([OH:22])=[C:4]([C:9](=O)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(C(C)C)CC)(C)C.[NH:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH2:40])=[NH:39])=[CH:36][CH:35]=1)[NH2:33]>CCO>[Br:1][C:2]1[C:3]([OH:22])=[C:4]([C:9](=[N:33][NH:32][C:34]2[CH:35]=[CH:36][C:37]([C:38]([NH2:40])=[NH:39])=[CH:41][CH:42]=2)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22556975HCID 22556975, compoundHCID 225569864-Hydrazinylbenzene-1-carboximidamide

Product 1

HCID 136411679HCID 136411679, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

For example, a solution of 1-(3-bromo-2-hydroxy-5-methyl-phenyl)-3-(4-nitro-phenyl)-propan-1-one 201 (1.48 g, 0.004 mol), EtOH (30 mL), diisopropylethylamine (Hunigs base)(3 mL), and 4-Hydrazino-benzamidine 200 (0.93 g, 0.004 mol) is heated at reflux for 4 hr. (reaction times can vary between 2 h to 18 h). The solution is cooled to ambient temperature, filtered, washed with 6N HCl (2×25 mL), and dried for 12-18 h in a vacuum oven to give a 90% yield of 4-{N′-[1-(3-bromo-2-hydroxy-5-methyl-phenyl)-3-(4-nitro-phenyl)-propylidene]-hydrazino}-benzamidine 202 as an off-white solid (1.78 g, 0.0036 mol).

Workup

  1. temperatureat reflux for 4 hr
  2. custom(reaction times can vary between 2 h to 18 h)
  3. filtrationfiltered
  4. washwashed with 6N HCl (2×25 mL)
  5. customdried for 12-18 h in a vacuum oven

Sources & evidence

ORD record
ord-f53fcb9b3edb4332b2c8abe7feaa84c6
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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