Sodium Bicarbonate → HCID 59828824, compound

HRID 1191090Notes

Reaction equation

HRID 1191090 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=1)=O.[CH:13]1([CH2:16][NH:17][C:18]([NH2:20])=[S:19])[CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>C(O)C>[CH:13]1([CH2:16][NH:17][C:18]2[S:19][CH:2]=[C:3]([C:5]3[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=3)[N:20]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2795339N-CyclopropylmethylthioureaHCID 58497180HCID 58497180, compound

Product 1

HCID 59828824HCID 59828824, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Slurry crude 6-(2-bromo-acetyl)-nicotinonitrile (5.2 g), cyclopropylmethyl-thiourea (2.7 g, 20.8 mmol) and sodium bicarbonate (1.95 g, 23.1 mmol) in ethanol (135 mL) at room temperature. Stir the mixture at reflux for 1 h under a nitrogen atmosphere. Cool the mixture to room temperature and concentrate in vacuo to a solid. Recrystallize from ethanol (20 mL) and water (100 mL) at 5° C. to obtain the desired intermediate as a tan solid (4.8 g, 81%). MS (ES+) m/z: 257 (M+H)+.

Workup

  1. customat room temperature
  2. temperatureat reflux for 1 h under a nitrogen atmosphere
  3. concentrationconcentrate in vacuo to a solid
  4. customRecrystallize from ethanol (20 mL) and water (100 mL) at 5° C.

Sources & evidence

ORD record
ord-0d193306e4ea42a1a8bbab0d6f0a5569
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…