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

반응식

HRID 15025 반응식
[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]

참가 물질

4

반응물 2

HCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 178488244HCID 178488244, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-321f1925f9ae4c01af76f2f17cfae4fa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732468B2

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