Triethylamine → 1-Ethyl-3-(5-fluoro-2-methylphenyl)-2-thioxo-imidazolidin-4-one

HRID 742250ノート

反応式

HRID 742250 の反応式
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:18])=[C:13]([N:15]=[C:16]=[S:17])[CH:14]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[CH2:4][C:5](=[O:7])[N:15]([C:13]2[CH:14]=[C:9]([F:8])[CH:10]=[CH:11][C:12]=2[CH3:18])[C:16]1=[S:17])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 316542N-EthylglycineHCID 5194435-Fluoro-o-tolyl Isothiocyanate

生成物 1

HCID 114252721-Ethyl-3-(5-fluoro-2-methylphenyl)-2-thioxo-imidazolidin-4-one収率 41.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of the crude N-ethyl glycine (11.5 g), 5-fluoro-2-methylphenylisothiocyanate (10.42 g), triethylamine (12.5 g) and chloroform (300 mL) was heated at reflux for 6 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (500 mL) and washed with water (500 mL). The organic phase was evaporated to dryness. The residue was dissolved in ethanol (50 mL), then diluted with diethyl ether (200 mL). The solution was saturated with hydrogen chloride. The mixture was filtered. The solid was discarded. The filtrate was evaporated to dryness. The residue was dissolved in diethyl ether (300 mL) and washed with water (200 mL). The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness. Crystallization from ethanol afforded the title compound (6.5 g) as a pink solid, m.p. 98°-100° C. Anal. Calcd. for. C12H13F N2O S: C, 57.13; H, 5.19; N, 11.10. Found: C, 56.88; H, 5.17; N, 11.05. Mass spectrum (EI, M.+) m/z 252.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  5. washwashed with water (500 mL)
  6. customThe organic phase was evaporated to dryness
  7. dissolutionThe residue was dissolved in ethanol (50 mL)
  8. additiondiluted with diethyl ether (200 mL)
  9. filtrationThe mixture was filtered
  10. customThe filtrate was evaporated to dryness
  11. dissolutionThe residue was dissolved in diethyl ether (300 mL)
  12. washwashed with water (200 mL)
  13. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  14. customevaporated to dryness
  15. customCrystallization from ethanol

出典と根拠

ORDレコード
ord-c7921eb47700433d90dd13b63bb6bf0c
出典データセット
uspto-grants-1996_09
特許番号
US05554607

反応ノート

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