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

HRID 6975

반응식

HRID 6975 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-084376ff6cbd402bbcddd99c0de3c3d7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084170B2

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