2-Aminothiophenol → HCID 15222259, compound

HRID 36850Notes

Reaction equation

HRID 36850 reaction equation
O[C:2]1[C:3](=[O:12])[N:4]([CH2:9][CH2:10][CH3:11])[C:5](=[O:8])[NH:6][CH:7]=1.BrN1C(=O)CCC1=O.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[SH:28]>C(O)C>[CH2:9]([N:4]1[C:3](=[O:12])[C:2]2[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28][C:7]=2[NH:6][C:5]1=[O:8])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 67184N-bromobutanimideHCID 15225229HCID 15225229, compound

Product 1

HCID 15222259HCID 15222259, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the 5-hydroxy-3-propylpyrimidine-2,4(1H,3H)-dione (0.85 g) in ethanol (40 ml), N-bromosuccinimide (0.98 g) was added in portions at room temperature. The mixture was stirred for 30 min. 2-Aminobenzenethiol (0.94 g) was added and the mixture was heated at reflux for one hour. After cooling, the precipitate was collected to give 1,5-dihydro-3-propyl-2H-pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione (1.20 g, 87% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. temperatureAfter cooling
  4. customthe precipitate was collected

Sources & evidence

ORD record
ord-39fdf17b5f5545aca2734a542994b75a
Source dataset
uspto-grants-1995_05
Patent number
US05418231

Reaction notes

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