HCID 12483030, compound → HCID 20548644, compound

HRID 1449344Notes

Reaction equation

HRID 1449344 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cs+].[CH3:11][N:12]([CH3:25])[C:13]([N:22]([CH3:24])[CH3:23])=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[N+:16]([CH3:18])[CH3:17]>C(O)C>[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][N:16]([CH3:17])[C:15]([N:19]([CH3:21])[CH3:20])=[CH:14][C:13]([N:22]([CH3:24])[CH3:23])=[N+:12]([CH3:25])[CH3:11]

Participants

4

Reactant 2

HCID 12483030HCID 12483030, compoundHCID 2368555217265-04-2

Product 1

HCID 20548644HCID 20548644, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.11 g (8.3 mmoles) of cesium benzoate in 45 ml of ethanol (dried over molecular sieves) was added to a slurry of 2.6 g (8.3 mmoles) of 3,3-bisdimethylamino-N,N,N',N'-tetramethylacrylamidinium perchlorate1 in 45 ml of dry ethanol. The resulting mixture was stirred overnight, filtered, and the filtrate evaporated to dryness at 35° C. To the residue dissolved in 10 ml of dry ethanol was added an additional 0.97 g of the perchlorate. The resulting mixture was stirred overnight, filtered, and the filtrate evaporated to dryness at 35° to yield 2.0 g of product, isolated as the hemihydrate.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness at 35° C
  3. dissolutionTo the residue dissolved in 10 ml of dry ethanol
  4. additionwas added an additional 0.97 g of the perchlorate
  5. stirringThe resulting mixture was stirred overnight
  6. filtrationfiltered
  7. customthe filtrate evaporated to dryness at 35°

Sources & evidence

ORD record
ord-3d23b935ab5842beb7247ad1edd5b620
Source dataset
uspto-grants-1980_02
Patent number
US04190598

Reaction notes

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