Meclofenamic Acid → 2-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide

HRID 1088290ノート

反応式

HRID 1088290 の反応式
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([Cl:15])[C:9]=1[NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](O)=[O:20].CN(C)C=O.[NH2:31][NH:32][C:33]([NH2:35])=[S:34]>C(Cl)Cl.N1C=CC=CC=1>[NH2:35][C:33](=[S:34])[NH:32][NH:31][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=1[NH:16][C:9]1[C:10]([Cl:15])=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=1[Cl:7]

参加物

7

反応物 4

HCID 4037Meclofenamic AcidHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2723789Thiosemicarbazide

生成物 1

HCID 98641092-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide収率 42.4%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Oxalyl chloride (2.85 g, 22.5 mmol) in 10 ml of methylene chloride is added dropwise to a 0° C. suspension of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoic acid (3.17 g, 10.6 mmol) and dimethylformamide (830 μl, 10.6 mmol) in 50 ml of methylene chloride. The clear yellow solution is stirred at 0° C. for 15 minutes and then at room temperature for 30 minutes. The solution is then concentrated in vacuo to give a yellow solid. This solid is added in portions to a suspension of thiosemicarbazide (1.95 g, 21.4 mmol) in 20 ml of pyridine. The suspension is stirred at 0° C. for 30 minutes then at room temperature overnight. The reaction mixture is concentrated in vacuo and the residue is partitioned between ethyl acetate and water. The organic layer is concentrated, then slurried with equal volumes of ethyl acetate and hexane. The off-white solid is collected by filtration providing 1.66 g (42%) of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl) hydrazide, mp is undefined.

後処理

  1. waitat room temperature for 30 minutes
  2. concentrationThe solution is then concentrated in vacuo
  3. customto give a yellow solid
  4. stirringThe suspension is stirred at 0° C. for 30 minutes
  5. customat room temperature
  6. customovernight
  7. concentrationThe reaction mixture is concentrated in vacuo
  8. customthe residue is partitioned between ethyl acetate and water
  9. concentrationThe organic layer is concentrated
  10. filtrationThe off-white solid is collected by filtration

出典と根拠

ORDレコード
ord-d7bc837529924ea693387075bf18c946
出典データセット
uspto-grants-1990_10
特許番号
US04962119

反応ノート

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