Water → 1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde

HRID 6772

反応式

HRID 6772 の反応式
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.CCN(CC)CC.O>CS(C)=O>[C:21]1([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:6]2[CH:7]=[C:3]([CH:2]=[O:1])[N:4]=[CH:5]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 962WaterHCID 8471TriethylamineHCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

生成物 1

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

The product from Step 8.a. (2.04 g, 6.00 mmol) was suspended in DMSO (10.0 ml) and Et3N (3.34 ml, 24.0 mmol) and SO3-pyridine complex (2.39 g, 15.0 mmol) were added at room temperature. The mixture was warmed at about 110° C. for about 1 hour and then allowed to cool. The mixture was poured into 150 ml H2O and the product was filtered off. The residue was treated with saturated NaHCO3 solution (50 ml) and extracted 2×100 ml CH2Cl2. The combined CH2Cl2 layers were washed with 5% citric acid solution (100 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was crystallized from MeOH and H2O. Yield=1.08 g (53%).

後処理

  1. temperatureto cool
  2. filtrationthe product was filtered off
  3. additionThe residue was treated with saturated NaHCO3 solution (50 ml)
  4. extractionextracted 2×100 ml CH2Cl2
  5. washThe combined CH2Cl2 layers were washed with 5% citric acid solution (100 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from MeOH and H2O

出典と根拠

ORDレコード
ord-2dd48e91d9f149d4ba76a652ed59e760
出典データセット
uspto-grants-2006_08
特許番号
US07084135B1

関連ノート

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