Ethanol → N-(6-chloro-2-naphthyl)carbamic acid ethyl ester

HRID 1270771노트

반응식

HRID 1270771 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](C(O)=O)[CH:6]=[CH:5]2.C([N:17]([CH2:20]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1.[CH2:39]([OH:41])[CH3:40]>O1CCOCC1>[CH2:39]([O:41][C:20](=[O:29])[NH:17][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[CH:8]=1)[CH3:40]

참가 물질

6

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 132883276-Chloronaphthalene-2-carboxylic acid

생성물 1

HCID 68803058N-(6-chloro-2-naphthyl)carbamic acid ethyl ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 6-chloro-2-naphthoic acid (1 g, 4.84 mmol) and triethylamine (1.35 mL, 9.68 mmol) in 1,4-dioxane (20 mL) at room temperature, is added DPPA (1.56 mL, 7.26 mmol). After stirring at room temperature for 2.5 hours, ethanol (2.82 mL, 48.4 mmol) is added and the reaction is heated to reflux temperature for 12 hours. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (3:1 hexanes/EtOAc) gives N-(6-chloro-2-naphthyl)carbamic acid ethyl ester as a white solid.

후처리

  1. temperaturethe reaction is heated
  2. temperatureto reflux temperature for 12 hours
  3. temperatureAfter cooling to room temperature
  4. customthe mixture is partitioned between EtOAc and water
  5. washThe organic layer is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by rotary evaporator
  8. customto give an oil

출처 및 근거

ORD 기록
ord-761ed3b65c7a4ce99bfd4fb4449fbdcb
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202364B2

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