Triethylamine → 1-(5-Acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea

HRID 1480

反応式

HRID 1480 の反応式
[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[NH:7][C:8](=[O:10])[CH3:9].C(N(CC)CC)C.[C:21]1([O:27]C(Cl)=O)C=CC=CC=1.[CH2:31]([NH2:34])[C:32]#[CH:33]>O1CCCC1.O.C(OCC)(=O)C>[C:8]([NH:7][C:6]1[C:5]([F:12])=[CH:4][C:3]([Cl:13])=[C:2]([NH:1][C:21]([NH:34][CH2:31][C:32]#[CH:33])=[O:27])[CH:11]=1)(=[O:10])[CH3:9]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 239041PropargylamineHCID 11769584N-(5-amino-4-chloro-2-fluorophenyl)acetamide

生成物 1

HCID 538737111-(5-Acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 5'-amino-4'-chloro-2'-fluoroacetanilide (11.25 g, 55.6 mmol), and triethylamine (7.70 mL, 55.6 mmol) in tetrahydrofuran is added dropwise to a stirred solution of phenylchloroformate (8.70 mL, 69.4 mmol) in tetrahydrofuran while maintaining the reaction mixture temperature at 25°-30° C. After the addition is complete, the reaction mixture is stirred at room temperature for 75 minutes, and poured into ethyl acetate. The organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a tan solid. A solution of the solid in tetrahydrofuran is treated with propargylamine (9.52 mL, 139 mmol), refluxed for 1 hour, and poured into water. The aqueous mixture is filtered to obtain a solid which is washed sequentially with water, 0.5N hydrochloric acid and water, and dried overnight to give the title product as a beige solid.

後処理

  1. temperaturewhile maintaining the reaction mixture temperature at 25°-30° C
  2. additionAfter the addition
  3. washThe organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a tan solid
  7. temperaturerefluxed for 1 hour
  8. filtrationThe aqueous mixture is filtered
  9. customto obtain a solid which
  10. washis washed sequentially with water, 0.5N hydrochloric acid and water
  11. customdried overnight

出典と根拠

ORDレコード
ord-5a556d937a384abda5eb0822445fcd79
出典データセット
uspto-grants-1998_03
特許番号
US05726126

関連ノート

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