Triethylamine → [4-(3,5-Dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl)amine

HRID 1062626Notes

Reaction equation

HRID 1062626 reaction equation
Br.Br[CH:3]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[CH:7]=1)=O.[NH2:20][C:21]([NH2:23])=[S:22].C(N(CC)CC)C>C(#N)C>[CH3:13][C:8]1[CH:7]=[C:6]([C:4]2[N:20]=[C:21]([NH2:23])[S:22][C:3]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:11]=[C:10]([CH3:12])[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 222823612-Bromo-1-(3,5-dimethylphenyl)-2-(4-pyridyl)ethanone hydrocbromide

Product 1

HCID 9925734[4-(3,5-Dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl)amineYield 55.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-1-(3,5-dimethylphenyl)-2-(4-pyridyl)ethanone hydrobromide (5.0 g, 13 mmol) and thiourea (1.0 g, 14 mmol) in acetonitrile (60 mL) was added dropwise triethylamine (1.9 ml, 14 mmol) and the mixture was stirred at room temperature for 3 h. The solvent was concentrated under reduced pressure and a saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with water and the solvent was evaporated. The obtained crude crystals were recrystallized from ethyl acetate to give the title compound (2.0 g, 7.2 mmol, yield 55%).

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogencarbonate solution was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customthe solvent was evaporated
  6. customThe obtained crude crystals
  7. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0d55bbe93c7542db9b24d264ab5f7419
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

Loading…