Triethylamine → HCID 9821613, compound

HRID 2212344Notes

Reaction equation

HRID 2212344 reaction equation
C(N(CC)CC)C.Br.Br[CH:10]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:22]=1)[C:11]([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)=O.[NH2:35][C:36]([NH2:38])=[S:37]>C(#N)C>[CH3:20][C:15]1[CH:14]=[C:13]([C:11]2[N:35]=[C:36]([NH2:38])[S:37][C:10]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)[CH:18]=[C:17]([CH3:19])[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 21964198HCID 21964198, compound

Product 1

HCID 9821613HCID 9821613, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (1.4 mL, 10 mmol) was added dropwise to a solution of 2-bromo-1-(3,5-dimethylphenyl)-2-(2-phenylmethyloxy-4-pyridyl)ethanone hydrobromide (4.8 g, 9.8 mmol) and thiourea (0.77 g, 11 mmol) in acetonitrile (40 mL) and the mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, a saturated aqueous solution of sodium hydrogencarbonate was added to the residue and extracted with ethyl acetate. The organic layer was washed with water, dried and the solvent was distilled off. The resulting crude crystals were recrystallized from ethyl acetate to obtain 2.0 g (5.2 mmol, yield 53%) of the title compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe resulting crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c3ab1b3dabe44fa6b83ac293c3b95bbf
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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