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4-Methoxyphenol → 1,3-Benzothiazol-2-yl[2-(4-methoxyphenoxy)pyrimidin-4-yl]acetonitrile

HRID 854266
Notes
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Reaction equation

HRID 854266 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15](Cl)[N:14]=1)[C:11]#[N:12].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([O:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[N:14]=1)[C:11]#[N:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 3952292-(Benzo[d]thiazol-2-yl)-2-(2-chloropyrimidin-4-yl)acetonitrile

Product 1

HCID 99514801,3-Benzothiazol-2-yl[2-(4-methoxyphenoxy)pyrimidin-4-yl]acetonitrileYield 51.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1 (0.300 g, 1.05 mmol) in DMSO (7 ml) were added 4-methoxyphenol (0.261 g, 2.1 mmol) and cesium carbonate (1.7 g, 5.25 mmol) and the suspension was shaken at 100° C. for 8 days. After cooling to r.t., the suspension was poured onto ice/water and the product was extracted with AcOEt. The organic phases were washed with water then brine, dried over MgSO4 and concentrated to dryness. The residue was triturated in hot EtOH then filtered off and dried under vacuum at 50° C. overnight, affording 202 mg (51%) of the title compound.

Workup

  1. temperatureAfter cooling to r.t.
  2. additionthe suspension was poured onto ice/water
  3. extractionthe product was extracted with AcOEt
  4. washThe organic phases were washed with water
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe residue was triturated in hot EtOH
  8. filtrationthen filtered off
  9. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-c9d37e517de4445288f3bc18717d29a9
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259162B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes