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

HRID 853204
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HRID 853204 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

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

생성물 1

HCID 878318102-Iodo-3-tetradecylthioacetylamino-1-triphenylmethyloxypropane수율 21%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e9cd72ba806f4867b91d5d9fb0a48916
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253296B2

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