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

HRID 32850ノート

反応式

HRID 32850 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 451216914-Ethylsulfanyl-thiazol-2-ylamine収率 71.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-dafbd9d12b564aecb50cf05e1f676174
出典データセット
uspto-grants-2008_09
特許番号
US07427635B2

反応ノート

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