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

HRID 1297179노트

반응식

HRID 1297179 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 reduced 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 under reduced pressure

출처 및 근거

ORD 기록
ord-580c9d00c6cd47ceb84475476bc6b7b8
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250430B2

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