Sodium Hydroxide → HCID 68893999, compound

HRID 1437460Notes

Reaction equation

HRID 1437460 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[NH2:15][C:16]1[CH:21]=[C:20]([Br:22])[CH:19]=[CH:18][C:17]=1[OH:23].[C:24](O)(=O)/[CH:25]=[CH:26]/[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[Na+]>CS(O)(=O)=O>[Br:22][C:20]1[CH:19]=[CH:18][C:17]2[O:23][C:24](/[CH:25]=[CH:26]/[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:15][C:16]=2[CH:21]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 3518402-Amino-4-BromophenolHCID 444539Cinnamic Acid

Product 1

HCID 68893999HCID 68893999, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus pentaoxide (2.84 g) was added to methanesulfonic acid (10 ml) and the mixture was stirred at 100° C. for 1 hour to give a solution. To the solution were added 2-amino-4-bromophenol (1.88 g) and trans-cinnamic acid (1.48 g), and the mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was poured onto ice, neutralized with an 8 N sodium hydroxide and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography. The fraction eluted with ethyl acetate-hexane (1:3, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to obtain 5-bromo-2-[(E)-2-phenylethenyl]benzoxazole (966 mg, 32%).

Workup

  1. customto give a solution
  2. stirringthe mixture was stirred at 100° C. for 1.5 hours
  3. additionThe reaction mixture was poured onto ice
  4. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. distillationThe solvent was distilled off under reduced pressure
  8. washThe fraction eluted with ethyl acetate-hexane (1:3
  9. concentrationv/v) was concentrated under reduced pressure
  10. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-330e1da8ac034912b9801a6c25c78aa6
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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