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

HRID 536046

반응식

HRID 536046 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-0f87bf007f8d43d0813b84f4291b22b7
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859571B2

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