Triethylamine → HCID 178465532, compound

HRID 1297508Notes

Reaction equation

HRID 1297508 reaction equation
C([O:5][C:6]1[C:7](=[O:24])[C:8](=O)[C:9]=1[CH:10]=[C:11]1[C:19]([CH3:21])([CH3:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH3:22])CCC.[N:25]#[C:26][NH2:27].[CH2:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH3:29]>C(O)C>[CH2:28]([NH+:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH3:29].[C:26]([N:27]=[C:8]1[C:7](=[O:24])[C:6]([O-:5])=[C:9]1[CH:10]=[C:11]1[C:19]([CH3:21])([CH3:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH3:22])#[N:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9864CyanamideHCID 58915119HCID 58915119, compound

Product 1

HCID 178465532HCID 178465532, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1 g (3.1 mmol) of 3-butoxy-4-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolylidenmethyl)-3-cyclobutene-1,2-dione (18), 200 mg (4.8 mmol) of cyanamide and 0.5 ml (3.6 mmol) of triethylamine is refluxed with stirring in 10 ml of absolute ethanol for 12 h. The solvent is removed under reduced pressure by a rotary evaporator. The obtained gum is column purified (Silica gel 60, 0–5% methanol-chloroform) to give triethylammonium-3-cyanimino-4-oxo-2-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolylidenmethyl)-1-cyclobuten -1-olate (19) as an oily, yellow solid. Yield: 0.96 g (78%).

Workup

  1. temperatureis refluxed
  2. customThe solvent is removed under reduced pressure by a rotary evaporator
  3. custompurified (Silica gel 60, 0–5% methanol-chloroform)

Sources & evidence

ORD record
ord-7e52ff4be6cc4eadb4e9bcba3b5faf0b
Source dataset
uspto-grants-2007_07
Patent number
US07250517B2

Reaction notes

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