4-Isopropoxyaniline → 4-[(4-Isopropoxyphenyl)amino]-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729286

反応式

HRID 729286 の反応式
Cl[C:2]1[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:19]([O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)([CH3:21])[CH3:20]>CC#N>[CH:19]([O:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:2]2[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:25][CH:24]=1)([CH3:21])[CH3:20]

参加物

4

反応物 2

HCID 821124-IsopropoxyanilineHCID 672431604-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

生成物 1

HCID 117110694-[(4-Isopropoxyphenyl)amino]-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide収率 59.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
160 °C

実験手順

4-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.2 g, 0.7 mmol), 4-isopropoxyaniline (0.106 g, 0.7 mmol) and TEA (0.071 g, 0.7 mmol) was dissolved in dry MeCN (3 ml). The reaction mixture was heated at 160° C. for 30 min in a microwave reactor. The solvent was evaporated and the residue was purified by silica gel column chromatography using a 70:30 mixture of heptane:EtOAc as eluant to give the title compound (0.166 g, 59%). 1H NMR (500 MHz, CDCl3): δ 7.21-7.15 (m, 1H), 7.13-7.09 (m, 4H), 7.06 (brs, 1H), 6.65-6.59 (m, 2H), 6.53-6.48 (m, 2H), 4.48 (hep, 1H), 4.35 (hep, 1H), 1.63 (d, 6H), 1.23 (d, 6H); 13C NMR (125 MHz, CDCl3): δ 159.0, 155.5, 131.6, 129.5, 128.9, 128.1, 125.0, 124.1, 124.0, 116.0, 109.7, 70.4, 47.8, 21.9, 20.4.

後処理

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography
  3. additiona 70:30 mixture of heptane

出典と根拠

ORDレコード
ord-88de4f35abf6439b96f76b2d0fd55a5b
出典データセット
uspto-grants-2009_09
特許番号
US07582629B2

関連ノート

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