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

HRID 1077869ノート

反応式

HRID 1077869 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 110032962-bromo-4-methylaminosulfonylmethyl-N-trifluoroacetylaniline収率 29.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-20822c68ef4f42b7a45c2dc86f9ada87
出典データセット
uspto-grants-1996_08
特許番号
US05545644

反応ノート

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