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Imidazole → 2-Iodo-3-tetradecylthioacetylamino-1-triphenylmethyloxypropane

HRID 853204
ノート
印刷プレビュー

反応式

HRID 853204 の反応式
[CH2:1]([CH2:15][C:16]([NH:18][CH2:19][CH:20](O)[CH2:21][O:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[S:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:67]I.S(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[I:67][CH:20]([CH2:19][NH:18][C:16](=[S:17])[CH2:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:21][O:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 23665763Sodium BisulfiteHCID 866032103-Tetradecylthioacetylamino-1-triphenylmethyloxypropan-2-ol

生成物 1

HCID 878318102-Iodo-3-tetradecylthioacetylamino-1-triphenylmethyloxypropane収率 21%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

3-tetradecylthioacetylamino-1-triphenylmethyloxypropan-2-ol (example 20a) (2 g, 3.31 mmol) was dissolved in toluene (100 ml). Imidazole (0.564 g, 8.28 mmol), triphenylphosphine (2.171 g, 8.28 mmol) and iodine (1.681 g, 6.62 mmol) were then added in that order. The reaction medium was stirred at room temperature for 20 hours. A saturated sodium bisulfite solution was added until complete blanching of the reaction medium. The phases were separated and the aqueous phase was extracted with toluene. The organic phases were combined, washed with saturated sodium chloride solution, dried on magnesium sulfate and filtered. The residue obtained after evaporation of the solvent (4.65 g) was purified by chromatography on silica gel (eluent: dichiromethane) to give the desired compound in the form of a yellow oil.

後処理

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with toluene
  3. washwashed with saturated sodium chloride solution
  4. customdried on magnesium sulfate
  5. filtrationfiltered
  6. customThe residue obtained
  7. customafter evaporation of the solvent (4.65 g)
  8. customwas purified by chromatography on silica gel (eluent: dichiromethane)

出典と根拠

ORDレコード
ord-e9cd72ba806f4867b91d5d9fb0a48916
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07253296B2

反応ノート

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