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

HRID 51299

反応式

HRID 51299 の反応式
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH:25]=[C:24]([CH:26]=[O:27])[N:23]=[CH:22]1.C(N(CC)CC)C.O>CN(C)C=O>[C:1]([N:21]1[CH:25]=[C:24]([CH:26]=[O:27])[N:23]=[CH:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 764281H-Imidazole-4-carbaldehyde

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of trityl chloride (9.5 g, 34.3 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to an ice-cooled solution of imidazole-4-carboxaldehyde (3 g, 31.2 mmol) and triethylamine (17 ml, 125 mmol) in N,N-dimethylformamide (30 ml) and the solution was stirred for 2 hours. The reaction was then allowed to warm to room temperature, and was stirred for a further 18 hours. Water (200 ml) was added, and the resulting pink solid was collected and dried, then dissolved in dichloromethane (200 ml). The resulting solution was washed with water (2×100 ml), dried (MgSO4) and evaporated under reduced pressure. The product was recrystallised from ethanol to afford the title compound as a solid, 7.8 g. 1H-NMR (CDCl3, 400 MHz) δ: 7.06 (m, 6H), 7.32 (m, 9H), 7.48 (s, 1H), 7.58 (s, 1H), 9.82 (s, 1H). Microanalysis found: C, 81.54; H, 5.37; N, 8.24. C23H18N2O requires C, 81.63; H, 5.36; N, 8.28%.

後処理

  1. stirringwas stirred for a further 18 hours
  2. customthe resulting pink solid was collected
  3. customdried
  4. dissolutiondissolved in dichloromethane (200 ml)
  5. washThe resulting solution was washed with water (2×100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe product was recrystallised from ethanol

出典と根拠

ORDレコード
ord-7e4a9f9166434d7ba8d06a2ed98ab35d
出典データセット
uspto-grants-2004_03
特許番号
US06713496B2

関連ノート

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