Bromine → 2-bromo-4-methylaminosulfonylmethyl-N-trifluoroacetylaniline

HRID 1077869노트

반응식

HRID 1077869 반응식
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)(=[O:5])=[O:4].C(=O)(O)[O-].[Na+].[Br:25]Br>CO.C(Cl)Cl>[Br:25][C:9]1[CH:8]=[C:7]([CH2:6][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])[CH:19]=[CH:18][C:10]=1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14]

참가 물질

6

반응물 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 199702154-Methylaminosulfonylmethyl-N-trifluoroacetylaniline

생성물 1

HCID 110032962-bromo-4-methylaminosulfonylmethyl-N-trifluoroacetylaniline수율 29.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

To a chilled suspension of 4-methylaminosulfonylmethyl-N-trifluoroacetylaniline(10.9 g) in methanol (100 mL) was added sodium bicarbonate (28 g), followed by bromine (18.3 g) in methylene chloride (30 mL). The reaction mixture was then diluted with methylene chloride (70 mL) and quenched by the addition of sodium sulfite (20 g), filtered through CELITE and concentrated in vacuo to a yellow residual solid. This solid was twice reslurried in methylene chloride (300 mL) then refiltered and the filtrates evaporated in vacuo. The residual materials were combined in 10% acetone/methylene chloride solution and concentrated then purified by column chromatography (eluting with 4% acetone in methylene chloride) to give the title compound (4.10g) mp 170° C.; TLC (methylene chloride/acetone 15:1) Rf=0.36, and the corresponding dibromide (5.56 g) TLC (methylene chloride/acetone 15:1) Rf=0.31.

후처리

  1. customquenched by the addition of sodium sulfite (20 g)
  2. filtrationfiltered through CELITE
  3. concentrationconcentrated in vacuo to a yellow residual solid
  4. customthe filtrates evaporated in vacuo
  5. concentrationconcentrated
  6. customthen purified by column chromatography (eluting with 4% acetone in methylene chloride)

출처 및 근거

ORD 기록
ord-20822c68ef4f42b7a45c2dc86f9ada87
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05545644

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