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Chlorotrimethylsilane → 1-(Triphenylmethyl)-1H-imidazole-4-propanoic acid

HRID 1167445
ノート
印刷プレビュー

反応式

HRID 1167445 の反応式
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:3]=[CH:2]1.C[Si](Cl)(C)C.C(N(CC)CC)C.Cl[C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.C(#N)C.CO>[C:25]1([C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:1]2[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:3]=[CH:2]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471Triethylamine2 回HCID 178525356HCID 178525356、化合物

生成物 1

HCID 74084421-(Triphenylmethyl)-1H-imidazole-4-propanoic acid収率 82.9%

試薬・触媒・溶媒 3

HCID 887Methanol
溶媒
HCID 6342Acetonitrile溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

3-(4-Imidazolyl)propionic acid (1.0 g, 7.1 mmol) was suspended in a mixture of dichloromethane (5 ml) and acetonitrile (25 ml). Trimethylsilyl chloride (781 mg, 7.2 nmmol) was added and the mixture refluxed for 4 hours. Triethylamine (1 ml) was added, and refluxing continued for 15 minutes. Cooled, triethylamine (1 ml) added followed by chlorotriphenylmethane (1.99 g, 7.1 mmol) in dichloromethane (10 ml), and the mixture stirred at ambient temperature for 2 hours. MeOH (20 ml) was added, the mixture stirred for 30 minutes, then evaporated to dryness. Water (50 ml) was added to the residue, and the pH adjusted to 8-8.5 with triethylamine. The precipitate was filtered off, washed with diethyl ether, and dried to give the desired product (2.25 g). MS (ESP): 383 (MH+) for C25H22N2O2;

後処理

  1. temperaturethe mixture refluxed for 4 hours
  2. temperaturerefluxing
  3. temperatureCooled
  4. stirringthe mixture stirred for 30 minutes
  5. customevaporated to dryness
  6. additionWater (50 ml) was added to the residue
  7. filtrationThe precipitate was filtered off
  8. washwashed with diethyl ether
  9. customdried

出典と根拠

ORDレコード
ord-ad6a48cc776640f1baf8c40bbc12dd69
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06617339B1

反応ノート

読み込み中…

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