Water → 1-(3-methylphenyl)-3-[4-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenyl]thiourea

HRID 1247462

反応式

HRID 1247462 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][NH:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[C:20]([N:24]=[C:25]=[S:26])[CH:19]=1.O>CN(C=O)C>[CH3:27][C:18]1[CH:19]=[C:20]([NH:24][C:25]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:9]=3[CH2:10][NH:11][C:12]4=[O:17])=[CH:6][CH:7]=2)=[S:26])[CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 962WaterHCID 69304m-TolylisothiocyanateHCID 219075114-(4-Aminophenyl)isoindolin-1-one

生成物 1

HCID 53298851-(3-methylphenyl)-3-[4-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenyl]thiourea収率 43.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of Example 1D (0.1 g, 0.44 mmol) in DMF (3 mL) was treated with m-tolylisothiocyanate (0.06 mL, 0.45 mmol), stirred at room temperature overnight, then cooled to 0° C., treated with water, and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 3% methanol/dichloromethane to give 72 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H); 4.53 (s, 2H); 6.96 (d, J=7.12 Hz, 1H); 7.23 (t, J=7.80 Hz, 1H); 7.29 (d, J=7.80 Hz, 2H); 7.57–7.69 (m, 7H); 8.68 (s, 1H); 9.84 (s, 1H); 9.88 (s, 1H); MS (ESI(−)) m/e 372 (M−H)−.

後処理

  1. temperaturecooled to 0° C.
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 3% methanol/dichloromethane

出典と根拠

ORDレコード
ord-45b1eb922cfc46a0bad5a5bf646e7a74
出典データセット
uspto-grants-2006_10
特許番号
US07129260B2

関連ノート

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