Lawesson's reagent → 5-(4,4-Dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile

HRID 1793357

反応式

HRID 1793357 の反応式
[CH3:1][C:2]1([CH3:21])[C:7]2[CH:8]=[C:9]([C:12]3[S:16][C:15]([C:17]#[N:18])=[CH:14][C:13]=3[CH3:19])[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=O)[O:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:21])[C:7]2[CH:8]=[C:9]([C:12]3[S:16][C:15]([C:17]#[N:18])=[CH:14][C:13]=3[CH3:19])[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[S:31])[O:3]1

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 98147685-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile

生成物 1

HCID 99729445-(4,4-Dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile収率 51.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile (5 g, 16.7 mmol) in anhydrous toluene was added, at room temperature under a blanket of nitrogen, Lawesson's reagent (6 g, 14.8 mmol). The reaction mixture was heated at reflux for 2 hrs, allowed to cool to room temperature, and solvent was removed in vacuo. The residue was purified by a silica gel column chromatography (THF:hexane/1:3) to yield the title compound as a yellowish solid (2.4 g, 46%): mp 211–212° C.; 1H-NMR (DMSO-d6) δ 12.3 (s, 1H), 7.88 (s, 1H), 7.46–7.52 (m, 2H), 7.16 (d, 1H, J=8.3 Hz), 2.30 (s, 3H), 1.68 (s, 6H); MS (ESI) m/z 313 [M−H]−; Anal. Calc. For C16H14N2OS2; C, 61.12; H, 4.49; N, 8.91. Found: C, 60.91; H, 4.48; N, 8.66.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hrs
  3. customsolvent was removed in vacuo
  4. customThe residue was purified by a silica gel column chromatography (THF:hexane/1:3)

出典と根拠

ORDレコード
ord-ab8530a118334e6b91e2f78ad5b520fd
出典データセット
uspto-grants-2006_07
特許番号
US07081457B2

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