Water → HCID 25260863, compound

HRID 1966202Notes

Reaction equation

HRID 1966202 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.[CH2:12]([O:14][C:15](=[O:20])[C:16](=O)[CH2:17]Br)[CH3:13].O>CN(C=O)C>[CH2:12]([O:14][C:15]([C:16]1[N:11]=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[S:10][CH:17]=1)=[O:20])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 66144Ethyl bromopyruvateHCID 23438874N-(5-Bromopyridin-2-yl)thiourea

Product 1

HCID 25260863HCID 25260863, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

(5-Bromo-pyridine-2-yl)-thiourea (1 mmol) is dissolved in DMF (2 ml) and 3-Bromo-2-oxo-propionic acid ethyl ester (1 eq.) is added and stirred 2 h at 70° C. The suspension is diluted with DMF (2 ml). After cooling to RT the reaction solution is poured into water and the resulting precipitate is filtered, washed with water and dried 16 h in vacuo at 40° C. “A4” is obtained as colourless powder in a yield of 78%; mp. 299.8-300.8° C.; HPLC (method C): 2.01 min; LC-MS (method A): 2.002 min, 327.95 (M+H+);

Workup

  1. temperatureAfter cooling to RT the reaction solution
  2. filtrationthe resulting precipitate is filtered
  3. washwashed with water
  4. dry with materialdried 16 h in vacuo at 40° C. “A4”
  5. customis obtained as colourless powder in a yield of 78%
  6. custom2.01 min
  7. custom2.002 min, 327.95 (M+H+)

Sources & evidence

ORD record
ord-0892a73dd1bc414889ed1cac52d3d923
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

Loading…