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Phenyl isocyanate → N-[2-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]-N'-phenylurea

HRID 499495
Notes
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Reaction equation

HRID 499495 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[N:16]=[C:15]([C:17]2[S:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21](=[O:23])[N:22]=2)[CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[C:34]1([N:40]=[C:41]=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(#N)C>[O:23]=[C:21]1[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[S:18][C:17]([C:15]2[N:16]=[C:11]([CH2:10][CH2:9][NH:8][C:41]([NH:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:42])[CH:12]=[CH:13][CH:14]=2)=[N:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 11430Potassium CarbonateHCID 684539582-[6-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750203N-[2-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]-N'-phenylureaYield 17.4%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A mixture of 2-[6-(2-aminoethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (0.40 g, 1.0 mmol), potassium carbonate (0.41 g, 3.0 mmol) and acetonitrile (15 ml) was stirred at room temperature for 20 minutes. Successively phenyl isocyanate (0.47 g, 4.0 mmol) was added to the mixture, and the mixture was refluxed for 4 hrs. After cooling, the precipitates were collected by filtration and dissolved in chlorobenzene and water. The organic layer was dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from hexane-chlorobenzene to give the titled compound (0.07 g, 17%) as pale yellow crystals.

Workup

  1. temperaturethe mixture was refluxed for 4 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitates were collected by filtration
  4. dissolutiondissolved in chlorobenzene
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was recrystallized from hexane-chlorobenzene

Sources & evidence

ORD record
ord-76a27287ad984ae3827bea7d873f1fe0
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes