Aniline → 2-Amino-6-methyl-N-phenylbenzamide

HRID 1625125

反応式

HRID 1625125 の反応式
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([OH:10])=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1C=CC=CC=1>[NH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:10]

参加物

5

反応物 3

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 1512106-Methylanthranilic acid

生成物 1

HCID 167877862-Amino-6-methyl-N-phenylbenzamide

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

Thionyl chloride (14.5 mL, 198 mmol) was added to a solution of 2-amino-6-methylbenzoic acid (10.0 g, 66.1 mmol) in benzene (250 mL). The resulting suspension was heated to reflux and stirred overnight. After cooling, the reaction was concentrated in vacuo, and the resulting residue was dissolved in chloroform (300 mL). Aniline (15 mL, 165 mmol) was added, and the mixture heated to reflux. After three hours, the reaction was allowed to cool and the resulting suspension was filtered. The filtrate was subjected to flash chromatography, and the crude product recrystallized from isopropanol to provide compound 15 as a yellow crystalline solid. MS (ES) m/z 227 (M+H), 134. 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.75 (d, 2H, J=7.9 Hz), 7.32 (t, 2H, J=7.8 Hz), 7.07 (t, J=7.3 Hz), 7.00 (t, 1H, J=7.8 Hz), 6.58 (d, 1H, J=8.1 Hz); 6.46 (d, 1H, J=7.4 Hz), 4.98 (br. s, 2H), 2.21 (s, 3H). The reaction described above and compound 15 are shown below.

後処理

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. concentrationthe reaction was concentrated in vacuo
  5. dissolutionthe resulting residue was dissolved in chloroform (300 mL)
  6. temperaturethe mixture heated to reflux
  7. waitAfter three hours
  8. temperatureto cool
  9. filtrationthe resulting suspension was filtered
  10. customthe crude product recrystallized from isopropanol

出典と根拠

ORDレコード
ord-fd8ca692d762486ea65df8a4d220efb0
出典データセット
uspto-grants-2014_07
特許番号
US08779131B2

関連ノート

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