4-Methyl-3-nitrobenzoyl chloride → 6-(4-Methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

HRID 15025

反応式

HRID 15025 の反応式
[NH2:1][N:2]1[C:6]([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=2)=[N:5][N:4]=[C:3]1[SH:19].[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>P(Cl)(Cl)(Cl)=O>[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]2[S:19][C:3]3=[N:4][N:5]=[C:6]([C:7]4[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=4)[N:2]3[N:1]=2)=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]

参加物

4

反応物 2

HCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 178488244HCID 178488244、化合物

生成物 1

HCID 249548716-(4-Methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole収率 87.9%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

A mixture of 4-amino-3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole (220 mg, 0.78 mmol) and 4-methyl-3-nitrobenzoyl chloride (156 mg, 0.78 mmol) in phosphoryl chloride (2 mL) was refluxed for 3 h. The solvent was evaporated and the residue was dissolved in dichloromethane (20 mL). It was neutralized by aqueous sodium carbonate. The organic layer was dried over sodium sulfate, and concentrated to give 293 mg (85%) of the title compound as solid. 1H NMR (CDCl3): 8.59 (d, J=2.1 Hz, 1H), 8.05-8.01 (dd, J=7.8, 1.8 Hz, 1H), 7.73 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 4.02 (s, 6H), 3.95 (s, 3H), 2.75 (s, 3H).

後処理

  1. temperaturewas refluxed for 3 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane (20 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-321f1925f9ae4c01af76f2f17cfae4fa
出典データセット
uspto-grants-2010_06
特許番号
US07732468B2

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