Acetic Acid → HCID 962168、化合物

HRID 2394267ノート

反応式

HRID 2394267 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[NH2:13].CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH2:1]([NH:13][C:12]1[CH:11]=[C:10]([Cl:9])[CH:16]=[C:15]([Cl:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 122813,5-DichloroanilineHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 962168HCID 962168、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A mixture of benzaldehyde (1.04 g, 9.40 mmol), 3,5-dichloroaniline (1.71 g, 10.60 mmol), and HOAc (0.20 mL) in MeOH (35 mL) was cooled to 0° C. Then a solution of NaBH3CN (28.0 mL, 28.0 mmol, 1.0 M solution in THF) was added dropwise via a syringe pump over 0.25 h. The solution was allowed to stir an additional 0.3 h at 0° C., and then room temperature for 18 h. The excess NaBH3CN was quenched with HCl and the solvent was removed under reduced pressure. The resulting oil was dissolved in EtOAc/H2O, basified with NaOH, and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The resulting oil was purified by chromatography (SiO2, 15:1 hexanes/EtOAc) to provide N-benzyl-3,5-dichloroaniline as a white solid. This compound was coupled to 2-chloro-4-trifluoromethylpyrimidine-5-carbonyl chloride as described and purified by chromatography (SiO2, 9:1 hexanes/EtOAc) to provide the title compound (15% yield) as a white foam; m.p. 102°-104° C.

後処理

  1. waitroom temperature for 18 h
  2. customThe excess NaBH3CN was quenched with HCl
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe resulting oil was dissolved in EtOAc/H2O
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customThe resulting oil was purified by chromatography (SiO2, 15:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-85e66fb94f494b538a8da48f76e7cf2d
出典データセット
uspto-grants-1998_09
特許番号
US05811428

反応ノート

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