Sodium Bicarbonate → HCID 59822270, compound

HRID 1191084Notes

Reaction equation

HRID 1191084 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9]Br)=[CH:4][N:3]=1.[CH:12]1([CH2:15][NH:16][C:17]([NH2:19])=[S:18])[CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[N:19]=[C:17]([NH:16][CH2:15][CH:12]3[CH2:14][CH2:13]3)[S:18][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2795339N-CyclopropylmethylthioureaHCID 108502672-bromo-1-(6-bromopyridin-3-yl)ethanone

Product 1

HCID 59822270HCID 59822270, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Slurry crude 2-bromo-5-(2-bromo-acetyl)-pyridine (11.5 g, ca. 48%), cyclopropylmethyl-thiourea (2.2 g, 16.9 mmol) and sodium bicarbonate (1.7 g, 20 mmol) in ethanol (100 mL) at room temperature. Stir the mixture at reflux for 1 h under a nitrogen atmosphere. Turn off heat and stir the mixture for 16 h at room temperature. Filter the slurry, then wash the solids with ethanol (50 mL), water (2×50 mL) and hexane (excess). Dry the solid in a vacuum oven for 20 h at 50° C. to obtain the desired intermediate as a tan solid (3.2 g, 61% over 2 steps). MS (ES+) m/z: 312 (M+2)+.

Workup

  1. customat room temperature
  2. temperatureat reflux for 1 h under a nitrogen atmosphere
  3. temperatureheat
  4. stirringstir the mixture for 16 h at room temperature
  5. filtrationFilter the slurry
  6. washwash the solids with ethanol (50 mL), water (2×50 mL) and hexane (excess)
  7. customDry the solid in a vacuum oven for 20 h at 50° C.

Sources & evidence

ORD record
ord-e46e4e0d076a4266bda7bb2bff7d17d0
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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