Water → HCID 25261015, compound

HRID 1966203Notes

Reaction equation

HRID 1966203 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)[CH2:15][O:16][C:17](=[O:19])[CH3:18].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]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[N:11]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 234388741-(5-Bromopyridin-2-yl)thiourea

Product 1

HCID 25261015HCID 25261015, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

(5-Bromo-pyridine-2-yl)-thiourea (1 mmol) is dissolved in DMF (2 ml) and acetic acid 3-chloro-2-oxo-propyl ester (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. “A5” is obtained as colourless powder in a yield of 82%; mp. 200.9-201.6° C.; HPLC (method C): 1.80 min; LC-MS (method A): 1.800 min, 327.95 (M+H+); 1H-NMR (DMSO-d6, 500 MHz): δ [ppm] 11.516 (s, 1H), 8.391 (d, 1H, J=2.4 Hz), 7.892 (dd, 1H, J=8.9 Hz, J=2.4 Hz), 7.020 (d, 1H, J=8.9 Hz), 6.998 (s, 1H), 5.015 (s, 2H), 2.062 (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. “A5”
  5. customis obtained as colourless powder in a yield of 82%
  6. custom1.80 min
  7. custom1.800 min, 327.95 (M+H+)

Sources & evidence

ORD record
ord-03f8c685e8054ad5a4d489fe0b320129
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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