Hexane → Ticlopidine

HRID 270660

반응식

HRID 270660 반응식
Br[CH2:2][CH2:3][C:4]1[S:5][CH:6]=[CH:7][C:8]=1[CH2:9]Br.[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].C(N(C(C)C)CC)(C)C.CCCCCC>C(#N)C.C(OCC)(=O)C>[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][N:15]1[CH2:2][CH2:3][C:4]2[S:5][CH:6]=[CH:7][C:8]=2[CH2:9]1

참가 물질

7

반응물 4

HCID 8058HexaneHCID 666482-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 693117222-(2-Bromoethyl)-3-(bromomethyl)thiophene

생성물 1

HCID 5472Ticlopidine수율 78%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

실험 절차

At below 5° C., 5.0 g of 2-(2-bromoethyl)-3-bromomethylthiophene obtained in Example 7 was dissolved in 50 mL of acetonitrile, and added thereto was a solution obtained by dissolving 2.7 g of 2-chlorobenzylamine and 6.8 g of diisopropylethylamine in 25 mL of acetonitrile. The resulting mixture was refluxed for 5 hours, and concentrated by evaporation under reduced pressure. The residue was dissolved in 100 mL of ethyl acetate, and washed twice with 70 mL portions of water. The organic layer was washed with 50 mL of saturated sodium chloride aqueous solution and concentrated under reduced pressure. The dark yellow colored oily residue thus obtained was subjected to a silica gel column chromatography (eluent, n-hexane:ethyl acetate=5:1) to obtain 3.6 g (yield of 78%) of the title compound as a yellowish oil.

후처리

  1. additionadded
  2. customobtained
  3. temperatureThe resulting mixture was refluxed for 5 hours
  4. concentrationconcentrated by evaporation under reduced pressure
  5. dissolutionThe residue was dissolved in 100 mL of ethyl acetate
  6. washwashed twice with 70 mL portions of water
  7. washThe organic layer was washed with 50 mL of saturated sodium chloride aqueous solution
  8. concentrationconcentrated under reduced pressure
  9. customThe dark yellow colored oily residue thus obtained

출처 및 근거

ORD 기록
ord-3dbc198f823c4ccca4c7a84853069b93
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449580B2

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