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Sodium Sulfate → 4-(3,5-Bis(trifluoromethyl)phenyl)thiazol-2-amine

HRID 644466
ノート
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反応式

HRID 644466 の反応式
[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[F:34][C:35]([F:50])([F:49])[C:36]1[CH:37]=[C:38]([C:46](=O)[CH3:47])[CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:58][C:59]([NH2:61])=[S:60].C(=O)([O-])O.[Na+]>O1CCCC1.C(O)C.O>[NH2:61][C:59]1[S:60][CH:47]=[C:46]([C:38]2[CH:37]=[C:36]([C:35]([F:50])([F:49])[F:34])[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=2)[N:58]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 24436Sodium SulfateHCID 1216161-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-oneHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 17977687Phenyltrimethylammonium bromide dibromide

生成物 1

HCID 27257694-(3,5-Bis(trifluoromethyl)phenyl)thiazol-2-amine
収率 83.3%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Phenyltrimethylammonium tribromide (753 mg, 2 mmol) was added to a solution of 3′,5′-bis(trifluoromethyl)acetophenone (0.51 g, 2.0 mmol) in tetrahydrofuran (5 mL) and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, ethanol (5 mL) and thiourea (152 mg, 2 mmol) were added to the residue obtained by evaporation of the solvent under reduced pressure, and the mixture was refluxed for 30 minutes. After the reaction mixture was cooled to room temperature, it was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) and washed with n-hexane under suspension to give the title compound (520.1 mg, 83.3%) as a light yellow white crystal.

後処理

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed with brine
  3. additionwere added to the residue
  4. customobtained by evaporation of the solvent under reduced pressure
  5. temperaturethe mixture was refluxed for 30 minutes
  6. temperatureAfter the reaction mixture was cooled to room temperature
  7. extractionextracted with ethyl acetate
  8. washAfter the ethyl acetate layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe residue obtained by evaporation of the solvent under reduced pressure
  11. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)
  12. washwashed with n-hexane under suspension

出典と根拠

ORDレコード
ord-6342840810324a33b69d42be3c897818
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700655B2

反応ノート

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