Methanesulfonyl chloride → N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide

HRID 2044099ノート

反応式

HRID 2044099 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17]>N1C=CC=CC=1>[N:18]1([C:16]([C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=2[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[O:17])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 60181686(2-Amino-4-nitrophenyl)(morpholin-4-yl)methanone

生成物 1

HCID 66833433N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide収率 14.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Methanesulfonyl chloride (0.179 mL, 2.302 mmol) was added to a solution of (2-amino-4-nitrophenyl)(morpholino)methanone (0.5783 g, 2.302 mmol) in pyridine (3 mL) at 0° C. After 30 min at 0° C., the pyridine solvent was evaporated under reduced pressure. The resulting brown oil was triturated with hot CH2Cl2 and filtered. The filtrate was concentrated and purified by silica gel chromatography, eluting with 30-100% EtOAc in hexanes, to give the expected product as yellow solid (108 mg, 14% yield). LCMS: (M+H)+=330.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.83 (1H, s), 8.24 (1H, d, J=2.26 Hz), 8.07 (1H, dd, J=8.41, 1.88 Hz), 7.61 (1 H, d, J=8.53 Hz), 3.69 (2H, d, J=4.02 Hz), 3.61 (2H, br. s.), 3.57 (2H, d, J=4.27 Hz), 3.16-3.22 (2H, m), 3.10 (3H, s).

後処理

  1. customthe pyridine solvent was evaporated under reduced pressure
  2. customThe resulting brown oil was triturated with hot CH2Cl2
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 30-100% EtOAc in hexanes

出典と根拠

ORDレコード
ord-c0fe81b619874200aa934a5a47c5ead1
出典データセット
uspto-grants-2013_11
特許番号
US08586751B2

反応ノート

読み込み中…