Lawesson's reagent → 4-(4,4-Dimethyl-2-thioxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-thiophene-2-carbonitrile

HRID 1258069

反応式

HRID 1258069 の反応式
[CH3:1][C:2]1([CH3:20])[O:7][C:6](=O)[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[C:15]([C:18]#[N:19])[S:16][CH:17]=3)=[CH:12][C:3]1=2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>CC1C=CC=CC=1C>[CH3:1][C:2]1([CH3:20])[O:7][C:6](=[S:30])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[C:15]([C:18]#[N:19])[S:16][CH:17]=3)=[CH:12][C:3]1=2

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 99436994-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-thiophene-2-carbonitrile

生成物 1

HCID 99044294-(4,4-Dimethyl-2-thioxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-thiophene-2-carbonitrile収率 35.4%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A mixture of 4-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-thiophene-2-carbonitrile (0.23 g, 0.8 mmol) and Lawesson's reagent (0.38 g, 0.96 mmol) in anhydrous o-xylene was heated to reflux under nitrogen for 3 hours. The solvent was removed in vacuo and the residue was purified by a flash chromatography (silica gel, hexane:ethyl acetate/3:1) to afford the title compound as a yellow solid (85 mg, 35%): mp 242-243° C.; 1H-NMR (DMSO-d6) δ 12.22 (s, 1H, D2O exchangeable), 8.50 (d, 1H, J=1.2 Hz), 8.37 (d, 1H, J=1.0 Hz), 7.71 (m, 2H), 7.09 (d, 1H, J=8.0 Hz), 1.69 (s, 6H); MS (APCI) m/z 301 ([M+H]+, 100%); Anal. Calcd. For C15H12N2OS2: C, 59.97; H, 4.03; N, 9.33. Found: C, 59.67; H, 3.85; N, 9.14.

後処理

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 3 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by a flash chromatography (silica gel, hexane:ethyl acetate/3:1)

出典と根拠

ORDレコード
ord-f0a55795e1db4809b22ffa0466ea61a0
出典データセット
uspto-grants-2013_06
特許番号
US08466146B2

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