Flufenamic Acid → HCID 15678604、化合物

HRID 1088292

反応式

HRID 1088292 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)=[C:5]([C:7](O)=[O:8])[CH:6]=1.[NH2:21][NH:22][C:23]([NH2:25])=[S:24]>O1CCCC1.N1C=CC=CC=1>[NH2:25][C:23](=[S:24])[NH:22][NH:21][C:7](=[O:8])[C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=1[NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1

参加物

5

反応物 2

HCID 3371Flufenamic AcidHCID 2723789Thiosemicarbazide

生成物 1

HCID 15678604HCID 15678604、化合物収率 44%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N,N'-Carbonyldiimidazole (4.56 g, 27.6 mmol) is added to a room temperature solution of flufenamic acid (5.07 g, 18.0 mmol) in 70 ml of tetrahydrofuran. The clear yellow solution is stirred at room temperature for three hours. The solution is then added via cannula to a suspension of thiosemicarbazide (3.41 g, 37.5 mmol) in 55 ml of pyridine. The suspension is heated at reflux overnight. The clear orange solution is concentrated in vacuo and the residue is partitioned between ethyl acetate and water. The organic layer is washed with water, dried over magnesium sulfate and concentrated. The resulting solid is slurried with a 1:3 mixture of ethyl acetate and hexane. The off-white solid is collected by filtration providing 2.80 g (44%) of 2-[(3-trifluoromethylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide.

後処理

  1. temperatureThe suspension is heated
  2. temperatureat reflux overnight
  3. concentrationThe clear orange solution is concentrated in vacuo
  4. customthe residue is partitioned between ethyl acetate and water
  5. washThe organic layer is washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. additionThe resulting solid is slurried with a 1:3 mixture of ethyl acetate and hexane
  9. filtrationThe off-white solid is collected by filtration

出典と根拠

ORDレコード
ord-84610cee270b43a19bc9ce033ecb0aa3
出典データセット
uspto-grants-1990_10
特許番号
US04962119

関連ノート

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