Dimethylformamide → 2-Chloro-1,3-benzoxazol-6-OL

HRID 2370487Notes

Reaction equation

HRID 2370487 reaction equation
S[C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.S(Cl)([Cl:14])=O.CN(C=O)C>>[Cl:14][C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178515778HCID 178515778, compound

Product 1

HCID 234412462-Chloro-1,3-benzoxazol-6-OLYield 68%

Conditions

Temperature
80 °C

Procedure

2-Mercapto-benzoxazol-6-ol (1 eq) was dissolved in thionyl chloride (10 eq). DMF (0.6 eq) was slowly added to this solution at room temperature. The mixture was heated to 80° C. and refluxed for 15 minutes. The reaction mixture was cooled to room temperature and the solvent was removed. The resulting solid was azeotroped three times with xylenes. The solid was dissolved in a 10% solution of THF in ethyl acetate and washed once with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried with anhydrous sodium sulfate, filtered, and the solvent removed. The solid was triturated with acetonitrile to yield pure product with a 68% yield. MH+=170.0.

Workup

  1. temperaturerefluxed for 15 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was removed
  4. customThe resulting solid was azeotroped three times with xylenes
  5. dissolutionThe solid was dissolved in a 10% solution of THF in ethyl acetate
  6. washwashed once with a saturated aqueous solution of sodium bicarbonate
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed
  10. customThe solid was triturated with acetonitrile
  11. customto yield pure product with a 68% yield

Sources & evidence

ORD record
ord-a6cb1956556d4032a150ad14c6428957
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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