Toluene → HCID 58460220, compound

HRID 1946490Notes

Reaction equation

HRID 1946490 reaction equation
[CH3:1][CH:2]([C:4]1[NH:8][C:7]2[CH2:9][CH2:10][C:11](=[O:12])[C:6]=2[N:5]=1)[CH3:3].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1.C1(C)C=CC=CC=1.[NH4+].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Cl:22][C:17]1[CH:16]=[C:15]([CH2:14][N:5]2[C:6]3[C:11](=[O:12])[CH2:10][CH2:9][C:7]=3[N:8]=[C:4]2[CH:2]([CH3:1])[CH3:3])[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

7

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 58460155HCID 58460155, compound

Product 1

HCID 58460220HCID 58460220, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Tetrabutylammonium bromide (520 mg, 1.614 mmol) was added to a stirred mixture of Intermediate 17 (530 mg) and 4-(bromomethyl)-1,2-dichlorobenzene (852 mg) in sodium hydroxide 20% aq. (5.16 mL) and Toluene (6 mL). The RM was stirred at room temp for 3 hours. An excess of sat NH4Cl aq. solution was added and the mixture was extracted with EtOAc (3×30 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica (100 g) using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (660 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×30 ml)
  2. customdried (hydrophobic frit)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on silica (100 g)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b5e11760710242839c93a8b5aafa5d4f
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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