Aniline → 1-(Benzo[c][1,2,5]thiadiazol-5-yl)propan-1-one

HRID 626236ノート

反応式

HRID 626236 の反応式
NC1C=CC=CC=1.O=[S:9](Cl)Cl.[NH2:12][C:13]1[CH:14]=[C:15]([C:20](=[O:23])[CH2:21][CH3:22])[CH:16]=[CH:17][C:18]=1[NH2:19]>C1(C)C=CC=CC=1>[N:19]1[S:9][N:12]=[C:13]2[CH:14]=[C:15]([C:20](=[O:23])[CH2:21][CH3:22])[CH:16]=[CH:17][C:18]=12

参加物

5

反応物 3

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 202165581-(3,4-Diaminophenyl)propan-1-one

生成物 1

HCID 896575531-(Benzo[c][1,2,5]thiadiazol-5-yl)propan-1-one収率 50%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of aniline (1.86 g, 20 mmol) in 50 mL of toluene was added SOCl2 (2.6 g, 22 mmol) dropwise at 0° C. and the mixture was then refluxed for 2 h. After cooling to rt, 1-(3,4-diaminophenyl)propan-1-one (1.65 g, 10 mmol) was added. The mixture was refluxed for 2 h, cooled, concentrated, and purified by flash chromatography to give the desired product (960 mg, 50%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.21 (d, J=9.2 Hz, 1H), 8.06 (d, J=9.2 Hz, 1H), 3.15 (q, J=7.2 Hz, 2H), 1.30 (t, J=7.2 Hz, 3H).

後処理

  1. temperaturethe mixture was then refluxed for 2 h
  2. temperatureThe mixture was refluxed for 2 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-3ca546ba55c9426c85daa1b8c54f3332
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

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