Hydrochloric Acid → HCID 21997459, compound

HRID 1977277Notes

Reaction equation

HRID 1977277 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[OH:23][C:24]1[CH:29]=[CH:28][C:27](C2SC(C3C=CC(C(O)=O)=CC=3)=NN=2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]Br.Cl>CN(C)C=O>[O:23]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[N:10][N:9]=2)=[CH:6][CH:7]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 135815284HCID 135815284, compoundHCID 135815286HCID 135815286, compound

Product 1

HCID 21997459HCID 21997459, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of a mixture of methyl 4-[5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]benzoate and 4-[5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]benzoic acid (2.0 g), potassium carbonate (14.6 g) and N,N-dimethylformamide (15 ml) was added 1,5-dibromopentane (10 ml) and the mixture was stirred at 100° C. (bath temperature) for 1.5 hours. The resulting mixture was neutralized by 0.1N hydrochloric acid and extracted with dichloromethane. The organic layer was washed with brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with n-hexane. The solid was collected by filtration and dried. To this compound was added phenol (1.43 g), potassium carbonate (2.10 g) and N,N-dimethylformamide (30 ml), and the mixture was stirred at 100° C. (bath temperature) for 20 hours. After cooling, the reaction mixture was poured into saturated sodium hydrogen carbonate aqueous solution. The resulting precipitate was collected by filtration, washed with water. To this compound was added tetrahydrofuran (20 ml), ethanol (20 ml) and 10% sodium hydroxide aqueous solution (2.6 ml). The mixture was refluxed for 1.5 hours. The reactor mixture was diluted with water, acidified with 1N hydrochloric acid (10 ml). The resulting precipitate was collected by filtration, washed with water, dried under reduced pressure to give 4-[5-[4-(5-phenoxy-n-pentyloxy) phenyl]-1,3,4-thiadiazol-2-yl]benzoic acid (2.47 g), that was used crude in the next reaction.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was triturated with n-hexane
  6. filtrationThe solid was collected by filtration
  7. customdried
  8. additionTo this compound was added phenol (1.43 g), potassium carbonate (2.10 g) and N,N-dimethylformamide (30 ml)
  9. stirringthe mixture was stirred at 100° C. (bath temperature) for 20 hours
  10. temperatureAfter cooling
  11. additionthe reaction mixture was poured into saturated sodium hydrogen carbonate aqueous solution
  12. filtrationThe resulting precipitate was collected by filtration
  13. washwashed with water
  14. additionTo this compound was added tetrahydrofuran (20 ml), ethanol (20 ml) and 10% sodium hydroxide aqueous solution (2.6 ml)
  15. temperatureThe mixture was refluxed for 1.5 hours
  16. additionThe reactor mixture was diluted with water
  17. filtrationThe resulting precipitate was collected by filtration
  18. washwashed with water
  19. customdried under reduced pressure

Sources & evidence

ORD record
ord-5e6e0f159cfa45b88f69b25b7a90d727
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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