5-Methylthiazole → HCID 9873766, compound

HRID 484586Notes

Reaction equation

HRID 484586 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][CH:15]=[C:14]([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:13]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:34][C:35]1[S:39][CH:38]=[N:37][CH:36]=1>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][CH:15]=[C:14]([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:13]=3)[CH:4]=2)[CH:36]=1

Participants

4

Reactant 2

HCID 1379805-MethylthiazoleHCID 10459203HCID 10459203, compound

Product 1

HCID 9873766HCID 9873766, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4 g of N-[3-(bromomethyl)phenyl]-3-(tetradecyloxy)benzeneacetamide and 3.84 g of 5-methylthiazole in 40 ml of toluene is refluxed for 1.5 hours under argon, cooled and the solvent evaporated to a residue. The residue is mixed with ether and the solid collected by centrifugation. The solid is washed several times with ether then dried by vacuum to give 4.3 g of the desired product as an off white powder, m.p. 125°-130° C.

Workup

  1. temperatureis refluxed for 1.5 hours under argon
  2. temperaturecooled
  3. customthe solvent evaporated to a residue
  4. additionThe residue is mixed with ether
  5. customthe solid collected by centrifugation
  6. washThe solid is washed several times with ether
  7. customthen dried by vacuum

Sources & evidence

ORD record
ord-46612b107db140598a14e1812f76d909
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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