Water → 1-chloro-N-ethyl-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

HRID 1289359ノート

反応式

HRID 1289359 の反応式
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1)(=[O:5])=[O:4].I[CH2:18][CH3:19].C([O-])([O-])=O.[K+].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Cl:1][CH2:2][S:3]([N:6]([CH2:18][CH3:19])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1)(=[O:4])=[O:5]

参加物

7

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

生成物 1

HCID 154053651-chloro-N-ethyl-N-(4-fluoro-3-nitrophenyl)methanesulfonamide収率 71.4%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide (5.93 g, 22.1 mmol), iodoethane (3.79 g, 24.3 mmol), tetrabutylammonium bromide (0.712 g, 2.21 mmol), and anhydrous K2CO3 (8.85 g, 64 mmol) in anhydrous dimethylformamide (40 mL) was stirred at room temperature. When the starting material had disappeared based on thin layer chromatography on silica (6 h), the reaction mixture was poured into water (200 mL) and extracted with CH2Cl2 (500 mL). The organic extract was washed with water (two times with 50 mL), dried (MgSO4), and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, 1-chlorobutane and diethyl ether 100:1 v/v eluent) to give 4.68 g of the title compound of Step B as a solid melting at 80°-83° C. 1H NMR (Me2SO-d6, 400 MHz): δ8.17 (dd,1H, J=6.75 and 2.7Hz), 7.85 (dd,1H, J=9.4 and 3 Hz), 7.69 (dd,1H, J=11 and 9 Hz), 5.25 (s,2H), 3.83 (q,2H), 1.04 (t,3H).

後処理

  1. customhad disappeared based on thin layer chromatography on silica (6 h)
  2. extractionextracted with CH2Cl2 (500 mL)
  3. extractionThe organic extract
  4. washwas washed with water (two times with 50 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 1-chlorobutane and diethyl ether 100:1 v/v eluent)

出典と根拠

ORDレコード
ord-653a02fbb4ca4595b9c3f4d389a808ad
出典データセット
uspto-grants-1998_05
特許番号
US05750471

反応ノート

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