Hydrochloric Acid → (E)-2-thiophen-2-yl-ethenesulfonic acid 2,4-dichloro-benzoylamide

HRID 1272074ノート

反応式

HRID 1272074 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(=O)([O-])[O-].[K+].[K+].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1/[CH:23]=[CH:24]/[S:25]([NH2:28])(=[O:27])=[O:26].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:28][S:25](/[CH:24]=[CH:23]/[C:19]1[S:18][CH:22]=[CH:21][CH:20]=1)(=[O:27])=[O:26])=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 666452,4-Dichlorobenzoyl chlorideHCID 149124362-(Thiophen-2-yl)ethene-1-sulfonamide

生成物 1

HCID 11990600(E)-2-thiophen-2-yl-ethenesulfonic acid 2,4-dichloro-benzoylamide収率 29%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

2,4-Dichlorobenzoyl chloride (53 μL, 0.375 mmol) was added to a mixture of potassium carbonate (69 mg, 0.5 mmol) and (E)-2-thiophen-2-yl-ethenesulfonic acid amide (47 mg, 0.25 mmol) in 1,4-dioxane (1.5 mL) at ambient temperature. The mixture was heated at 80° C. for 16 hours then allowed to cool to room temperature whereupon 1N HCl (2 mL) was added in one portion. The mixture was extracted with ethyl acetate (2 mL) and the organics were dried with MgSO4, filtered and concentrated in vacuo. The resultant residue was purified by preparative HPLC to afford (E)-2-thiophen-2-yl-ethenesulfonic acid 2,4-dichloro-benzoylamide (26.3 mg, 29%).

後処理

  1. additionwas added in one portion
  2. extractionThe mixture was extracted with ethyl acetate (2 mL)
  3. dry with materialthe organics were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-18323cd34c984bd0b4c02c03498bb157
出典データセット
uspto-grants-2007_04
特許番号
US07208506B2

反応ノート

読み込み中…