Diphenylmethane → [(2-Diphenylmethylthio-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetic acid

HRID 2228689Notes

Reaction equation

HRID 2228689 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[O:15][CH2:16][C:17]([O:19]CC)=[O:18])[C:5]=2[N:6]=1.[C:22]1([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[C:22]1([CH:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[S:1][C:2]2[S:3][C:4]3[CH2:14][CH2:13][C:12]4[C:7](=[CH:8][CH:9]=[CH:10][C:11]=4[O:15][CH2:16][C:17]([OH:19])=[O:18])[C:5]=3[N:6]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 7580DiphenylmethaneHCID 11430Potassium CarbonateHCID 178472952Ethyl[(2-mercapto-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy)acetate

Product 1

HCID 9912063[(2-Diphenylmethylthio-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetic acidYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl [(2-mercapto-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetate (1.10 g, 3.42 mmol) in N,N-dimethylformamide (20 mL) were added diphenylmethane hromide (0.93 g, 3.76 mmol) and potassium carbonate (0.52 g, 3.76 mmol), and the mixture was stirred at 60° C. for 3 hours. This reaction mixture was diluted with ethyl acetate and water and, after phase separation, the aqueous layer was extracted with ethyl acetate. The pooled organic solution was washed with water, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in acetic acid (20 mL). To this solution was added concentrated sulfuric acid (10 ml), and the mixture was refluxed for 1 hour. After cooling, the reaction mixture was diluted with water and extracted with 2 portions of ethyl acetate. The pooled extract was washed with water, dried over MsGO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from hexane-ethyl acetate to provide 0.58 g of the title compound. Yield 37%.

Workup

  1. customafter phase separation
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe pooled organic solution was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in acetic acid (20 mL)
  8. additionTo this solution was added concentrated sulfuric acid (10 ml)
  9. temperaturethe mixture was refluxed for 1 hour
  10. temperatureAfter cooling
  11. additionthe reaction mixture was diluted with water
  12. extractionextracted with 2 portions of ethyl acetate
  13. extractionThe pooled extract
  14. washwas washed with water
  15. customdried over MsGO4
  16. filtrationfiltered
  17. concentrationThe filtrate was concentrated under reduced pressure
  18. customthe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-87e5cee553dc416f843a8808443bf4b4
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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