Acetic Acid → HCID 59255370, 화합물

HRID 77956

반응식

HRID 77956 반응식
[Cl:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12]N)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)(=[O:18])C.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 592553974-(5-Chloro-furan-2-ylmethyl)-benzylamine

생성물 1

HCID 59255370HCID 59255370, 화합물수율 44%

시약·촉매·용매 2

HCID 962Water용매3회HCID 8857Ethyl Acetate용매2회

실험 절차

To a mixture of 4-(5-chloro-furan-2-ylmethyl)-benzylamine (2.6 g) described in Manufacturing Example 62-1-2, acetic acid (25 mL) and water (25 mL) was added sodium nitrite (9.8 g, 140 mmol) at 0° C., which was stirred for 40 minutes at room temperature. Water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. Methanol (25 mL) was added to the residue at 0° C., followed by addition of potassium carbonate (3.3 g, 24 mmol) at the same temperature. This was stirred for 1 hour at the same temperature. Water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride, and the organic layer was concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:2) to obtain the title compound (1.2 mg, 44%).

후처리

  1. extractionto extract the reaction mixture
  2. washThe organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. customthe solvent was evaporated under a reduced pressure
  4. additionMethanol (25 mL) was added to the residue at 0° C.
  5. stirringThis was stirred for 1 hour at the same temperature
  6. extractionto extract the reaction mixture
  7. washThe organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride
  8. concentrationthe organic layer was concentrated under a reduced pressure
  9. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:2)

출처 및 근거

ORD 기록
ord-b830fde3e44e46abb7b31483d65f18e2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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