p-Toluenesulfonic acid → N-[4-bromo-2-chlorobenzoyl]-5-bromothiophene-2-sulfonamide

HRID 6975

反応式

HRID 6975 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([Cl:11])[CH:3]=1.[Br:12][C:13]1[S:17][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:14]=1.CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:21][S:18]([C:16]2[S:17][C:13]([Br:12])=[CH:14][CH:15]=2)(=[O:20])=[O:19])=[O:8])=[C:4]([Cl:11])[CH:3]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 1088294-Bromo-2-chlorobenzoic acidHCID 12413045-Bromo-2-thiophenesulfonamide

生成物 1

HCID 22019517N-[4-bromo-2-chlorobenzoyl]-5-bromothiophene-2-sulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

An 8 mL reaction vial is charged with 4-bromo-2-chlorobenzoic acid (0.39 mmol, 1.5 eq) and 2.0 mL of dichloromethane. A stock solution (4.0 mL) containing 5-bromothiophene-2-sulfonamide (0.26 mmol, 1 eq) and N,N-[dimethyl]-4-aminopyridine (48 mg, 0.39 mmol, 1.5 eq) in dichloromethane is added, followed by 0.261 g carbodiimide polystyrene resin (2.0 mmol/g, 0.52 mmol, 2.0 eq, Novabiochem) and the vial is capped and shaken. After 72 hr, 0.77 g sulphonated polystyrene resin (MP-TsOH) is added (1.53 mmol/g, 1.17 mmol, Argonaut). After about 18 hr the reaction mixture is filtered and concentrated under reduced pressure. Chromatography was applied to the residue and fractions containing product were combined and concentrated under reduce pressure to provide the title compound.

後処理

  1. customAn 8 mL reaction
  2. additionis added
  3. customthe vial is capped
  4. filtrationAfter about 18 hr the reaction mixture is filtered
  5. concentrationconcentrated under reduced pressure
  6. additioncontaining product
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-084376ff6cbd402bbcddd99c0de3c3d7
出典データセット
uspto-grants-2006_08
特許番号
US07084170B2

関連ノート

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