Trifluoroacetic acid → 4-Ethylsulfanyl-thiazol-2-ylamine

HRID 32850노트

반응식

HRID 32850 반응식
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([S:13][CH2:14][CH3:15])[N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:14]([S:13][C:11]1[N:12]=[C:8]([NH2:7])[S:9][CH:10]=1)[CH3:15]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 45117850tert-butyl N-(4-ethylsulfanyl-1,3-thiazol-2-yl)carbamate

생성물 1

HCID 451216914-Ethylsulfanyl-thiazol-2-ylamine수율 71.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(4-Ethylsulfanyl-thiazol-2yl)-carbamic acid tert-butyl ester (0.583 g, 2.24 mmole) was dissolved in methylene chloride (9 mL) and the resulting solution was cooled in an ice-water bath. Trifluoroacetic acid (5 mL) was added dropwise to this solution. The solution was stirred under an argon atmosphere for 3 hours, allowing the cooling bath to slowly warm up. At the conclusion of the reaction, the bath temperature was 12° C. The reaction was concentrated. The residue was redissolved in methylene chloride and concentrated. This was repeated two additional times to remove most of the trifluoroacetic acid. Following the final concentration, the residue was dissolved again in methylene chloride and washed with saturated sodium bicarbonate, water and brine. The organic phase was dried over sodium sulfate and concentrated to yield 4-ethylsulfanyl-thiazol-2-ylamine (0.256 g, 65%).

후처리

  1. temperaturethe resulting solution was cooled in an ice-water bath
  2. temperatureto slowly warm up
  3. customAt the conclusion of the reaction
  4. customwas 12° C
  5. concentrationThe reaction was concentrated
  6. dissolutionThe residue was redissolved in methylene chloride
  7. concentrationconcentrated
  8. customto remove most of the trifluoroacetic acid
  9. concentrationconcentration
  10. dissolutionthe residue was dissolved again in methylene chloride
  11. washwashed with saturated sodium bicarbonate, water and brine
  12. dry with materialThe organic phase was dried over sodium sulfate
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dafbd9d12b564aecb50cf05e1f676174
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427635B2

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