Triethylamine → HCID 21264604, compound

HRID 567121Notes

Reaction equation

HRID 567121 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]([CH3:15])[C:13]#[N:14].[C:20](OC)(=[O:23])[CH2:21][SH:22].C(N(CC)CC)C>C(O)C>[CH3:15][N:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][O:4][C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[CH3:1])[C:13]1[S:22][CH2:21][C:20](=[O:23])[N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 21264593HCID 21264593, compound

Product 1

HCID 21264604HCID 21264604, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.3 g (0.01 mol) of 40% pure N-[2-(2-methylphenoxymethyl)-phenyl]-N-methyl-cyanamide, 1.1 g (0.01 mol) of methyl thioglycolate and 0.15 g of triethylamine in 100 ml of ethanol is heated under reflux for 18 hours. The mixture is concentrated and the residue is chromatographed over silica gel using cyclohexane/ethyl acetate (1:3). 1.4 g (43% of theory) of 2-{methyl-[2-(2-methylphenoxymethyl)-phenyl]-amino}-thiazol-4-one are obtained.

Workup

  1. temperatureunder reflux for 18 hours
  2. concentrationThe mixture is concentrated
  3. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-c0d6ba87bc544e85a7bf2dc64060ed03
Source dataset
uspto-grants-2001_01
Patent number
US06177459B1

Reaction notes

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