Hydrochloric Acid → HCID 21997495, compound

HRID 1977276Notes

Reaction equation

HRID 1977276 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.OC1C=CC(C2SC(C3C=CC(C(O)=O)=CC=3)=NN=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].[O:50]([CH2:57][CH2:58][CH2:59][CH2:60]Br)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.Cl>CN(C)C=O>[O:50]([CH2:57][CH2:58][CH2:59][CH2:60][O: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]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 70986(4-Bromobutoxy)benzeneHCID 135815284HCID 135815284, compoundHCID 135815286HCID 135815286, compound

Product 1

HCID 21997495HCID 21997495, 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 (600 mg), potassium carbonate (531 mg) and N,N-dimethylformamide (3 ml) was added 4-phenoxybutylbromide (880 mg) and the mixture was stirred at 100° C. (bath temperature) for 2 hours. After cooling, the mixture was added to 0.1N hydrochloric acid (100 ml). The resulting precipitate was collected by filtration and washed with water. To this material was added tetrahydrofuran (20 ml), ethanol (20 ml) and 10% sodium hydroxide aqueous solution (1.39 ml). The mixture was refluxed for 2 hours. After cooling, the reaction mixture was diluted with water (100 ml), adjusted to pH 1.8 with 1N hydrochloric acid, then extracted with a mixture of dichloromethane (1000 ml), tetrahydrofuran (200 ml) and methanol (200 ml). 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 acetonitrile. The solid was collected by filtration and dried to give 4-[5-[4-(4-phenoxybutyloxy)phenyl]-1,3,4-thiadiazol-2-yl]benzoic acid (685 mg).

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. additionTo this material was added tetrahydrofuran (20 ml), ethanol (20 ml) and 10% sodium hydroxide aqueous solution (1.39 ml)
  5. temperatureThe mixture was refluxed for 2 hours
  6. temperatureAfter cooling
  7. additionthe reaction mixture was diluted with water (100 ml)
  8. extractionextracted with a mixture of dichloromethane (1000 ml), tetrahydrofuran (200 ml) and methanol (200 ml)
  9. washThe organic layer was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvents were removed under reduced pressure
  12. customthe residue was triturated with acetonitrile
  13. filtrationThe solid was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-c929cd6ba2aa43188769e6a091d38d7f
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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