3,4-Dimethylpyridine → HCID 15030146, compound

HRID 2227079Notes

Reaction equation

HRID 2227079 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:33])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[N:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[C:36]([CH3:41])[CH:35]=1>C(#N)C>[Br-:1].[CH3:41][C:36]1[CH:35]=[N+:34]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][C:10](=[O:33])[CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH:13]=3)[CH:4]=2)[CH:39]=[CH:38][C:37]=1[CH3:40]

Participants

4

Reactant 2

HCID 114173,4-DimethylpyridineHCID 10052253N-[3-(Bromomethyl)phenyl]-4-(tetradecyloxy)-benzeneacetamide

Product 1

HCID 15030146HCID 15030146, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.5 g of N-[3-(bromomethyl)phenyl]-4-(tetradecyloxy)benzeneacetamide and 933.5 mg of 3,4-lutidine in 25 ml of acetonitrile is refluxed under argon for 4 hours. The solvent is evaporated and the residue mixed with ether. The solid is collected via centrifugation, washed with ether several times and vacuum dried to give 1.5 g of the desired product as a gray-white powder, m.p. 125°-128° C.

Workup

  1. temperatureis refluxed under argon for 4 hours
  2. customThe solvent is evaporated
  3. additionthe residue mixed with ether
  4. customThe solid is collected via centrifugation
  5. washwashed with ether several times and vacuum
  6. customdried

Sources & evidence

ORD record
ord-bffdc6555984477d88bf04d51de34f0e
Source dataset
uspto-grants-1994_09
Patent number
US05350759

Reaction notes

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