Triethylamine → 2-Thiazolamine, 4-(4-methoxyphenyl)-N-methyl-5-(3-pyridinyl)-

HRID 1167649Notes

Reaction equation

HRID 1167649 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].Br.Br[CH:8]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O.C(N(CC)CC)C>C(#N)C>[CH3:1][NH:2][C:3]1[S:4][C:8]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723704MethylthioureaHCID 114633362-Bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 30248932-Thiazolamine, 4-(4-methoxyphenyl)-N-methyl-5-(3-pyridinyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of N-methylthiourea (242 mg) in acetonitrile (18 mL), was added 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide (1.0 g) and then triethylamine (0.4 mL) was added slowly dropwise to the mixture. After addition, the resulting mixture was stirred at reflux for 3 h, and the solvent was evaporated. An aqueous saturated solution of sodium hydrogen carbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried, and the solvent was evaporated. The crystalline residue was recrystallized from ethyl acetate-isopropyl ether to afford the title compound (650 mg, yield 85%).

Workup

  1. additionAfter addition
  2. temperatureat reflux for 3 h
  3. customthe solvent was evaporated
  4. additionAn aqueous saturated solution of sodium hydrogen carbonate was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. customdried
  8. customthe solvent was evaporated
  9. customThe crystalline residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-def5ad6195574d988d9aeff8e2556877
Source dataset
uspto-grants-2003_09
Patent number
US06620825B1

Reaction notes

Loading…