Water → 3-Amino-4-(2,5-dimethylphenylthio)benzonitrile

HRID 1946838ノート

反応式

HRID 1946838 の反応式
O.O.[Sn](Cl)Cl.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[S:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[N+:23]([O-])=O.CCOC(C)=O.O>CCO.Cl>[NH2:23][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:15]=1[S:14][C:8]1[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]=1[CH3:6])[C:19]#[N:20]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 291067464-(2,5-Dimethylphenylthio)-3-nitrobenzonitrile

生成物 1

HCID 435183713-Amino-4-(2,5-dimethylphenylthio)benzonitrile収率 74%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of Tin (II) chloride dihydrate (25.218 g, 112.0 mmol) in EtOH (85.0 mL) and conc. HCl (12 M, 15.0 mL) was stirred at 70° C. until a clear solution was formed. Compound 24 (8.0 g, 28.14 mmol) was then added over 10 min. The solution was kept slightly refluxing during addition. The reaction was monitored with TLC (25% EtOAc in hexanes, Rf=0.65). The reaction was complete after refluxing for 1.5 hrs as indicated by the absence of the starting material (TLC). Water (35 mL) was added and the resulting solution was allowed to cool to room temperature. Precipitation occurred during cooling. The mixture was further cooled and stirred for 30 min at 15° C. The precipitate was filtered, washed with water, and dried under vacuum to yield compound 25 as a white solid (5.30 g, 95% HPLC purity, 65% yield). 1H NMR (500 MHz, DMSO-d6): δ 7.20 (d, J=8 Hz, 1H), 7.07 (d, J=2 Hz, 1H), 7.04 (d, J=8 Hz, 1H), 7.00 (d, J=8 Hz, 1H), 6.90 (dd, J1=2 Hz, J2=8 Hz, 1H), 6.85 (s, 1H), 5.72 (s, 2H), 2.26 (s, 3H), 2.18 (s, 3H).

後処理

  1. customwas formed
  2. temperatureThe solution was kept slightly refluxing during addition
  3. temperatureafter refluxing for 1.5 hrs
  4. temperatureto cool to room temperature
  5. customPrecipitation
  6. temperatureduring cooling
  7. temperatureThe mixture was further cooled
  8. stirringstirred for 30 min at 15° C
  9. filtrationThe precipitate was filtered
  10. washwashed with water
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-b516554e25584908affacdb05b48b2f3
出典データセット
uspto-grants-2013_03
特許番号
US08399456B2

反応ノート

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