Benzenesulfonyl chloride, 4-chloro-3-nitro- → Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-

HRID 536046

反応式

HRID 536046 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[CH3:16][NH2:17]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:17][CH3:16])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

参加物

5

反応物 2

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 6364545Methylamine hydrochloride

生成物 1

HCID 67301Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-収率 65.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-chloro-3-nitrobenzenesulfonyl chloride (10 g, 39.1 mmol) in THF (100 mL) was cooled to −40° C. before being treated with a solution of methylamine hydrochloride (2.64 g, 39.1 mmol) in 10 ml of water followed by TEA (5.44 mL, 39.1 mmol). The reaction mixture was stirred and allowed to warm to room temperature over 1 hour before being partitioned between 350 mL EtOAc and 30 mL brine. The organic layer was washed twice with brine, dried over MgSO4 and subjected to flash chromatography (330 g silica gel, 0-40% EtOAc/hexane) to afford 4-chloro-N-methyl-3-nitrobenzenesulfonamide (6.38 g, 65%) as a light yellow solid. MS (m/z) 251.0 (M+H+).

後処理

  1. custombefore being partitioned between 350 mL EtOAc and 30 mL brine
  2. washThe organic layer was washed twice with brine
  3. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-0f87bf007f8d43d0813b84f4291b22b7
出典データセット
uspto-grants-2014_10
特許番号
US08859571B2

関連ノート

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