3,5-Bis(trifluoromethyl)benzaldehyde → N-(2-Bromo-4-methyl-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine

HRID 2075040

反応式

HRID 2075040 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH2:13][NH2:14].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH:20]=O.[B-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([F:11])([F:12])[F:10])=[CH:4][C:3]=1[CH2:13][NH:14][CH2:20][C:19]1[CH:22]=[C:23]([C:25]([F:27])([F:28])[F:26])[CH:24]=[C:17]([C:16]([F:15])([F:29])[F:30])[CH:18]=1

参加物

7

反応物 4

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 516892Sodium BicarbonateHCID 23676153Sodium bis(acetyloxy)boranuidyl acetateHCID 58968640Benzenemethanamine, 2-bromo-4-methyl-5-(trifluoromethyl)-

生成物 1

HCID 58968728N-(2-Bromo-4-methyl-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine収率 98.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of (2-bromo-4-methyl-5-(trifluoromethyl) phenyl) methanamine (189 mg, 0.705 mmol) and 3,5 bistrifluoromethyl benzaldehyde (170 mg, 0.705 mmol) in anhydrous toluene (10 mL) was heated under reflux for 3 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (25 mL). Sodium triacetoxyborohyride (373.5 mg, 1.76 mmol) was added and the mixture was stirred for 18 hours at room temperature. The mixture was poured into a mixture of saturated NaHCO3 (50 mL) and ethyl acetate (50 mL) and stirred for 30 minutes. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was dried with anhydrous sodium sulfate, filtered and concentrated to give the title compound (98.4%). 1H NMR (400 MHz, CDCl3) δ 7.83 (s, 2H) 7.76(s, 1H) 7.58(s, 1H) 7.41 (s, 1H) 3.92(s, 2H) 3.89(s, 2H) 2.44(s, 3H)

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane (25 mL)
  5. stirringstirred for 30 minutes
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  8. dry with materialThe combined organic layer was dried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-c6127e5008244144bd721a51c9cefc98
出典データセット
uspto-grants-2011_04
特許番号
US07919506B2

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