Triethylamine → HCID 23446833, 화합물

HRID 1841648노트

반응식

HRID 1841648 반응식
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:16]=[CH:15][C:9]([CH:10](O)[C:11]([OH:13])=O)=[CH:8][CH:7]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:29][CH2:30][NH2:31])[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]#[CH:28].C(N(CC)CC)C>C1(C)C=CC=CC=1.N1C=CC=CC=1.C(OCC)C.O1CCOCC1.O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]([Cl:3])[C:11]([NH:31][CH2:30][CH2:29][C:21]2[CH:22]=[CH:23][C:24]([O:25][CH2:26][C:27]#[CH:28])=[C:19]([O:18][CH3:17])[CH:20]=2)=[O:13])=[CH:15][CH:16]=1

참가 물질

10

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 97930p-Bromomandelic acidHCID 114705242-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine

생성물 1

HCID 23446833HCID 23446833, 화합물

시약·촉매·용매 5

HCID 1049Pyridine촉매HCID 962Water용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

실험 절차

To a mixture of thionyl chloride (3.7 g, 31 mmol) in toluene (10 ml) containing 3 drops of pyridine is added 4-bromomandelic acid (2.9 g, 13 mmol) in diethylether (40 ml). The reaction mixture is refluxed for 2 hours. The solvent is removed and the residue is co-evaporated with toluene. Subsequently the residue is dissolved in dioxane (20 ml) and added to 2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine (2.2 g, 11 mmol) and triethylamine (1.0 g, 10 mmol) in dioxane (20 ml). The resulting mixture is stirred for 16 hours, diluted with water (100 ml) and extracted with ethyl acetate (2×200 ml). The combined organic layer is washed with brine (150 ml), dried over magnesium sulfate and evaporated. 2-(4-Bromo-phenyl)-2-chloro-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide is obtained which is purified by chromatography on silica gel using ethyl/acetate/hexane as eluent. 1H-NMR (300 MHz, CDCl3): 2.53(t, 1H, C≡CH), 2.82(t, 2H, CH2CH2), 3.60(t, 2H, CH2CH2), 3.87(s, 3H, OCH3), 4.79(d, 2H, OCH2), 5.29(s, 1H, CHCl), 6.70-7.48(m, 8H, CH arom., NH).

후처리

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. customThe solvent is removed
  3. dissolutionSubsequently the residue is dissolved in dioxane (20 ml)
  4. extractionextracted with ethyl acetate (2×200 ml)
  5. washThe combined organic layer is washed with brine (150 ml)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

출처 및 근거

ORD 기록
ord-2758c5cdac2f4ac2b640206709b83fcc
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683211B1

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