Toluene → HCID 14677197, compound

HRID 486822Notes

Reaction equation

HRID 486822 reaction equation
[OH-].[Na+].[C:3]1([CH3:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[NH:11]1[CH:15]=[C:14]([C:16]2([CH2:25][OH:26])[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17]2)[N:13]=[CH:12]1.C(Cl)C1C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:9]([N:11]1[CH:15]=[C:14]([C:16]2([CH2:25][OH:26])[CH2:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:24]2)[N:13]=[CH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 178479666HCID 178479666, compound

Product 1

HCID 14677197HCID 14677197, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

0,0237 g of tetrabutylammonium bromide, 1 ml of 48% NaOH, 5 ml of toluene, 0,58 g of [2,3-dihydro-2-(1H-imidazol-4-yl)-1H-inden-2-yl]methanol hydrochloride prepared according to example 9a and 0,30 g of benzyl chloride were combined. The mixture was stirred for 2 h at 60°-70° C. Then the mixture was cooled and water was added, toluene was evaporated and the aqueous solution was made acidic while cooling simultaneously. The acid solutation was washed with ether and the product separated as an oily layer. The product was extracted in methylene chloride as hydrochloride.

Workup

  1. temperatureThen the mixture was cooled
  2. customtoluene was evaporated
  3. temperaturewhile cooling simultaneously
  4. washThe acid solutation was washed with ether
  5. customthe product separated as an oily layer
  6. extractionThe product was extracted in methylene chloride as hydrochloride

Sources & evidence

ORD record
ord-1bb3ca93fc424d3a995ad0090c13c785
Source dataset
uspto-grants-1994_03
Patent number
US05292887

Reaction notes

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