Flufenamic Acid → HCID 15678604, 화합물

HRID 1088292

반응식

HRID 1088292 반응식
[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

참가 물질

5

반응물 2

HCID 3371Flufenamic AcidHCID 2723789Thiosemicarbazide

생성물 1

HCID 15678604HCID 15678604, 화합물수율 44%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-84610cee270b43a19bc9ce033ecb0aa3
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04962119

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