p-Toluenesulfonic acid → HCID 178491344, compound

HRID 254461

Reaction equation

HRID 254461 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=O.[NH2:13][CH:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1/[CH:5]=[N:13]/[CH:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 777023-Pentanamine, 2,4-dimethyl-HCID 964042,6-Dimethoxybenzaldehyde

Product 1

HCID 178491344HCID 178491344, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 25.0 g (150 mmol) 2,6-dimethoxybenzaldehyde, 19.1 g (165 mmol) 3-amino-2,4-dimethylpentane and 0.500 g p-toluenesulfonic acid in 100 ml toluene was heated in a Dean-Stark apparatus to reflux for 2 hours. Then the cooled reaction mixture was washed with aqueous NaHCO3 solution, brine dried over Na2SO4, filtered and evaporated. The crude product was filtered through a silica pad with heptane/ethyl acetate 2:1 as eluent: 22.0 g [1-(2,6-dimethoxy-phenyl)-meth-(E)-ylidene]-(1-isopropyl-2-methyl-propyl)-amine as slightly yellow crystals: MS (EI): 264.3 ((M+H)+.), 262.3 ((M-H)+.), 248.3 ((M−CH3)+.), 220.2 ((M−(CH3)2CH)+.), 100%).

Workup

  1. temperaturewas heated in a Dean-Stark apparatus
  2. temperatureto reflux for 2 hours
  3. customThen the cooled reaction mixture
  4. washwas washed with aqueous NaHCO3 solution, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe crude product was filtered through a silica pad with heptane/ethyl acetate 2:1 as eluent

Sources & evidence

ORD record
ord-d89bcb139b314bc49a6166f783772c3f
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Linked notes

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