Chloroform → [(1,3-Diphenyl-5-propylpyrazol-4-yl)methyl]butylamine

HRID 1643189ノート

反応式

HRID 1643189 の反応式
S(Cl)(Cl)=O.[C:5]1([N:11]2[C:15]([CH2:16][CH2:17][CH3:18])=[C:14]([CH2:19]O)[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Cl)(Cl)Cl>C=CCCC>[C:5]1([N:11]2[C:15]([CH2:16][CH2:17][CH3:18])=[C:14]([CH2:19][NH:11][CH2:5][CH2:6][CH2:7][CH3:8])[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 227280971,3-Diphenyl-4-hydroxymethyl-5-propylpyrazole

生成物 1

HCID 20777201[(1,3-Diphenyl-5-propylpyrazol-4-yl)methyl]butylamine

試薬・触媒・溶媒 1

HCID 80041-Pentene溶媒

反応条件

温度
60 °C

実験手順

Thionyl chloride (1 mL) is added to a solution of 165 (289 mg) in pentene stabilized chloroform (8 mL) and the mixture heated to 60° C. for 2 hours. The resulting mixture is cooled, washed with saturated sodium bicarbonate solution, dried (Na2SO4), and concentrated. The resulting crude chloride is taken up in dimethylformamide (3 mL) and added dropwise to a solution of butylamine (1.0 g) in dimethylformamide (10 mL) containing 2g of powdered potassium carbonate. After the addition is complete, the resulting mixture is stirred for an additional 3 h and partitioned between water (20 mL) and ether (10 mL). The ether layer is washed 2 times with water, dried (Na2SO4), and concentrated. The resulting material is purified by chromatography on silica eluting with 10% CH3OH/CHCl3 to give the desired secondary amine 166. LC-MS (M+1): 348.3; 1H NMR (δ, CDCl3), 7.87 (dd, J=8.0, 1.6 Hz, 2H), 7.32-7.48 (m, 1H), 3.77 (s, 2H), 2.70 (m, 4H), 1.48 (m, 4H), 1.34 (m, 2H), 0.91 (t, J=7.6 Hz, 3H), 0.87 (t, J=7.6 Hz, 3H) ppm.

後処理

  1. temperatureThe resulting mixture is cooled
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. additionadded dropwise to a solution of butylamine (1.0 g) in dimethylformamide (10 mL)
  6. additioncontaining 2g of powdered potassium carbonate
  7. additionAfter the addition
  8. custompartitioned between water (20 mL) and ether (10 mL)
  9. washThe ether layer is washed 2 times with water
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customThe resulting material is purified by chromatography on silica eluting with 10% CH3OH/CHCl3

出典と根拠

ORDレコード
ord-ef1ed9e2ca9f4445b336282970718468
出典データセット
uspto-grants-2012_02
特許番号
US08119665B2

反応ノート

読み込み中…