Water → 7-Chloro-1H-pyrido[2,3-b][1,4]thiazin-2(3H)-one

HRID 1618673Notes

Reaction equation

HRID 1618673 reaction equation
[SH:1][CH2:2][C:3]([O:5]CC)=O.O.[OH-].[Na+].Cl[C:12]1[C:17]([NH2:18])=[CH:16][C:15]([Cl:19])=[CH:14][N:13]=1>CCO>[Cl:19][C:15]1[CH:14]=[N:13][C:12]2[S:1][CH2:2][C:3](=[O:5])[NH:18][C:17]=2[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12185Ethyl ThioglycolateHCID 14798Sodium HydroxideHCID 27999993-Amino-2,5-dichloropyridine

Product 1

HCID 672845567-Chloro-1H-pyrido[2,3-b][1,4]thiazin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 2-mercaptoacetate (2.0 mL, 18.4 mmol) in water (5.03 mL, 12.27 mmol) was added NaOH (0.491 g, 12.27 mmol). The reaction was stirred at rt for 10 min. After this time a solution of 2,5-dichloropyridin-3-amine (2.0 g, 12.27 mmol) in EtOH (20 mL) was added and the reaction was heated at reflux for 4 days and cooled to rt. The resulting precipitate was filtered and washed with hexanes (50 mL) and MeOH (5 mL) to give 7-chloro-1H-pyrido-[2,3-b][1,4]thiazin-2(3H)-one as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.76 (1H, d, J=0.6 Hz), 8.15 (1H, d, J=2.2 Hz), 7.31 (1H, d, J=2.3 Hz), 3.59-3.74 (2H, m). Mass Spectrum (ESI) m/e=201.0 (M+1).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 days
  3. temperaturecooled to rt
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with hexanes (50 mL) and MeOH (5 mL)

Sources & evidence

ORD record
ord-197ee2d786dd4c1980f754dac572a367
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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