Water → HCID 25260860, compound

HRID 1966201Notes

Reaction equation

HRID 1966201 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.[Br:12][CH2:13][C:14]([CH2:16]Br)=O.O>CN(C=O)C>[Br:12][CH2:13][C:14]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:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 699521,3-Dibromo-2-propanoneHCID 23438874N-(5-Bromopyridin-2-yl)thiourea

Product 1

HCID 25260860HCID 25260860, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

(5-Bromo-pyridine-2-yl)-thiourea (2.5 mmol) is dissolved in DMF (5 ml) and 1,3-dibromacetone (1 eq.) is added and stirred 2 h at 70° C. 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. After column chromatography (ethyl acetate/methanol) (4-bromomethyl-thiazole-2-yl)-(5-bromo-pyridine-2-yl)-amine is obtained as a colourless powder with a yield of 16%. HPLC (method C): 1.92 min; LC-MS (method A): 1.977 min, 347.95 (M+H+); 1H-NMR (DMSO-d6, 300 MHz): δ [ppm] 11.583 (s, 1H), 8.391 (d, 1H, J=2.4 Hz), 7.902 (dd, 1H, J=2.4 Hz, J=8.9 Hz), 7.119 (s, 1H), 7.023 (d, 1H, J=8.9 Hz), 4.622 (s, 2H).

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe resulting precipitate is filtered
  3. washwashed with water
  4. customdried 16 h in vacuo at 40° C

Sources & evidence

ORD record
ord-d37a82a3816f4c21a7e904062e6d3465
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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