Diisopropylethylamine → HCID 178516940、化合物

HRID 853005ノート

反応式

HRID 853005 の反応式
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[S:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=S.CCN(C(C)C)C(C)C>C(#N)C>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:12]1[S:11][CH2:17][C:15](=[O:16])[N:14]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 1399092-Chloro-4-fluorobenzylamineHCID 1201546Rhodanine

生成物 1

HCID 178516940HCID 178516940、化合物収率 16.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-chloro-4-fluoro-benzylamine (4.5 g, 28.19 mmol) and Rhodanine (3.75 g, 28.2 mmol) in acetonitrile (170 mL) was added DIPEA (9.82 mL, 56.4 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (8.42 g, 31.02 mmol) was added in two portions within 10 min. After addition, the suspension was allowed to warm to room temperature and stirred for 3 days. The resulting black solids were filtered through a plug of celite and washed with acetonitrile (1.0 L) and ethyl acetate (500 mL). The combined filtrates were removed under the vacuum and the crude residue was dissolved in ethyl acetate (150 mL) and washed with water and brine solution. After drying over magnesium sulfate, the filtrate was removed under the vacuum and the residue was dissolved in ethyl acetate (50 mL) at hot condition. After cooling in the refrigerator overnight, the solids were collected by filtration and washed with hexanes. After drying in air, 1.2 g (16.5% yield) of 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one was isolated as a white amorphous solid: EI-HRMS m/e calcd for C10H8FN2OS2 (M+) 258.0030, found 258.0027.

後処理

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. filtrationThe resulting black solids were filtered through a plug of celite
  4. washwashed with acetonitrile (1.0 L) and ethyl acetate (500 mL)
  5. customThe combined filtrates were removed under the vacuum
  6. dissolutionthe crude residue was dissolved in ethyl acetate (150 mL)
  7. washwashed with water and brine solution
  8. dry with materialAfter drying over magnesium sulfate
  9. customthe filtrate was removed under the vacuum
  10. dissolutionthe residue was dissolved in ethyl acetate (50 mL) at hot condition
  11. temperatureAfter cooling in the refrigerator overnight
  12. filtrationthe solids were collected by filtration
  13. washwashed with hexanes
  14. customAfter drying in air

出典と根拠

ORDレコード
ord-574ba6643c4240908437a799bd0fab8d
出典データセット
uspto-grants-2007_08
特許番号
US07253285B2

反応ノート

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