Diethyl Ether → HCID 10008954, compound

HRID 1647568Notes

Reaction equation

HRID 1647568 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.[CH3:34][C:35]1[S:39][CH:38]=[N:37][CH:36]=1.CCOCC>C1(C)C=CC=CC=1>[Br-:1].[CH3:34][C:35]1[S:39][CH:38]=[N+:37]([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:36]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1379805-MethylthiazoleHCID 10052253N-[3-(Bromomethyl)phenyl]-4-(tetradecyloxy)-benzeneacetamide

Product 1

HCID 10008954HCID 10008954, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.6 g of N-[3-(bromomethyl)phenyl]-4-(tetradecyloxy)benzeneacetamide and 3.46 g of 5-methylthiazole in 25 ml of toluene is refluxed under inert gas for 1.5 hours, cooled and poured into 200 ml of ether. The organic layer is decanted and the solid washed with ether and collected to give 3.8 g of the desired product as a white solid, m.p. 173°-175° C.

Workup

  1. temperatureis refluxed under inert gas for 1.5 hours
  2. temperaturecooled
  3. customThe organic layer is decanted
  4. washthe solid washed with ether
  5. customcollected

Sources & evidence

ORD record
ord-e430f64cf36b49d39d64383474af9c05
Source dataset
uspto-grants-1995_07
Patent number
US05432189

Reaction notes

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