5-Methylthiazole → HCID 10100347, compound

HRID 484579Notes

Reaction equation

HRID 484579 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1.[CH3:34][C:35]1[S:39][CH:38]=[N:37][CH:36]=1>C1(C)C=CC=CC=1.CCOCC>[Br-:1].[CH3:34][C:35]1[S:39][CH:38]=[N+:37]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([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:5][CH:4]=2)[CH:36]=1

Participants

5

Reactant 2

HCID 1379805-MethylthiazoleHCID 10346457HCID 10346457, compound

Product 1

HCID 10100347HCID 10100347, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.5 g of N-[4-(bromomethyl)phenyl]-4-(tetradecyloxy)benzeneacetamide and 2.69 g of 5-methylthiazole in 45 ml of toluene is refluxed under argon for 6 hours, then allowed to stand at ambient temperature overnight. The mixture is diluted with ether then evaporated to a residue which is dissolved in hot tetrahydrofuran and again diluted with ether. The solid is collected by centrifugation and washed with ether several times then dried under vacuum to give 1.9 g of the product as a white powder, m.p. 120°-125° C.

Workup

  1. temperatureis refluxed under argon for 6 hours
  2. customthen evaporated to a residue which
  3. dissolutionis dissolved in hot tetrahydrofuran
  4. additionagain diluted with ether
  5. customThe solid is collected by centrifugation
  6. washwashed with ether several times
  7. customthen dried under vacuum

Sources & evidence

ORD record
ord-a9fa5d333bad4f09a11a51c30ac5b986
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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