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

HRID 1067437

反応式

HRID 1067437 の反応式
C([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:8]=1[CH2:9][CH2:10][C:11]1[S:15][C:14]([SH:16])=[N:13][C:12]=12)C.[Br-].[C:23]1([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[C:23]1([CH:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[S:16][C:14]2[S:15][C:11]3[CH2:10][CH2:9][C:8]4[C:17](=[CH:18][CH:19]=[CH:20][C:7]=4[O:6][CH2:5][C:4]([OH:3])=[O:21])[C:12]=3[N:13]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 18470978Diphenylmethane bromideHCID 178472952Ethyl[(2-mercapto-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy)acetate

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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 bromide (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 MgSO4, 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%.

後処理

  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. dry with materialdried over MgSO4
  16. filtrationfiltered
  17. concentrationThe filtrate was concentrated under reduced pressure
  18. customthe residue was crystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-1ee74087afcb47eb89f80ce997e4c234
出典データセット
uspto-grants-2001_06
特許番号
US06248766B1

関連ノート

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