Water → HCID 25260858, compound

HRID 1966200Notes

Reaction equation

HRID 1966200 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.Cl[CH2:13][C:14](=O)[CH3:15].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:13]=[C:14]([CH3:15])[N:11]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6571ChloroacetoneHCID 23438874N-(5-Bromopyridin-2-yl)thiourea

Product 1

HCID 25260858HCID 25260858, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

1.2 (5-Bromo-pyridine-2-yl)-thiourea (1 mmol) is dissolved in DMF (2 ml) and 1-Chloro-propane-2-one (1 eq.) in DMF (2 ml) 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. (5-Bromo-pyridine-2-yl)-(4-methyl-thiazole-2-yl)-amine is obtained as a colourless powder in a yield of 86%; mp. 241.5-242.6° C.; HPLC (method C): 1.55 min, 269.95 (M+H+); LC-MS (method A): 1.432 min; 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 11.314 (s, 1H), 8.363 (d, 1H, J=2.9 Hz), 7.865 (dd, 1H, J=2.9 Hz, J=8.9 Hz), 7.037 (d, 1H, J=8.9 Hz), 6.578 (s, 1H), 2.242 (s, 3H).

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. (5-Bromo-pyridine-2-yl)-(4-methyl-thiazole-2-yl)-amine
  5. customis obtained as a colourless powder in a yield of 86%
  6. custom1.55 min, 269.95 (M+H+)
  7. custom1.432 min

Sources & evidence

ORD record
ord-152de537abd64c4d8479eee6cf21972c
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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