Toluene → HCID 58460143, compound

HRID 1946501Notes

Reaction equation

HRID 1946501 reaction equation
[CH3:1][C:2]([C:5]1[NH:9][C:8]2[CH2:10][CH2:11][C:12](=[O:13])[C:7]=2[N:6]=1)([CH3:4])[CH3:3].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.C1(C)C=CC=CC=1.[NH4+].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:6]2[C:7]3[C:12](=[O:13])[CH2:11][CH2:10][C:8]=3[N:9]=[C:5]2[C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 58460205HCID 58460205, compound

Product 1

HCID 58460143HCID 58460143, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Tetrabutylammonium bromide (317 mg) was added to a stirred mixture of Intermediate 32 (350 mg), 4-chlorobenzyl bromide (444 mg) in sodium hydroxide 15% aq. (10 mL) and toluene (15 mL). The RM was stirred at room temp under nitrogen atm. for 16 hours. Sat. NH4Cl aq. solution (10 mL) was added and the mixture was extracted with EtOAc (2×50 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum The residue was purified on silica (50 g) using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (421 mg). LC/MS MH+ 303, Rt 2.51 min (5 minute run).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×50 ml)
  2. customdried (hydrophobic frit)
  3. concentrationconcentrated under vacuum The residue
  4. customwas purified on silica (50 g)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aedfc60f6ed7497f8581a78cfedc2f7a
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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