4-Nitrophenol → 4-Nitrophenyl 2-chloropyridine-3-sulphonate

HRID 1384201

反応式

HRID 1384201 の反応式
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[C:16]([S:17](Cl)(=[O:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)([O-:23])=[O:22]>CN(C=O)C.C(OCC)(=O)C>[Cl:10][C:11]1[C:16]([S:17]([O:30][C:27]2[CH:28]=[CH:29][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=2)(=[O:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1

参加物

6

反応物 3

HCID 9804-NitrophenolHCID 81531DiisopropylethylamineHCID 102199682-Chloropyridine-3-sulfonyl chloride

生成物 1

HCID 211862554-Nitrophenyl 2-chloropyridine-3-sulphonate収率 66.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N,N-Diisopropylethylamine (0.45 ml) was added to a solution of 2-chloropyridine-3-sulphonyl chloride (0.53 g) and 4-nitrophenol (0.35 g) in DMF (5 ml). The mixture was stirred at ambient temperature for 30 minutes then diluted with ethyl acetate (25 ml) and washed with water (2×25 ml), saturated sodium carbonate solution (3×20 ml), water (20 ml) and saturated sodium chloride solution. Aqueous layers were back-extracted with ethyl acetate (25 ml) and the organic layers were combined and dried (MgSO4). Volatile material was removed by evaporation to give 4-nitrophenyl 2-chloropyridine-3-sulphonate (0.52 g) as a solid, m.p. 127-128° C.; 1H NMR (d6-DMSO): 7.5 (d, 2H), 7.7 (dd, 1H), 8.3 (d, 2H), 8.4 (dd, 1H), 8.8 (dd, 1H); mass spectrum (+ve FAB, NBA/DMSO): 315 (M+H)+.

後処理

  1. washwashed with water (2×25 ml), saturated sodium carbonate solution (3×20 ml), water (20 ml) and saturated sodium chloride solution
  2. extractionAqueous layers were back-extracted with ethyl acetate (25 ml)
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation

出典と根拠

ORDレコード
ord-fd3e5d02127e4480a88d5659d2499970
出典データセット
uspto-grants-2001_07
特許番号
US06258817B1

関連ノート

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