Thionyl Chloride → 4-Acetoxy-3-methoxy-cinnamic acid azide

HRID 597653

반응식

HRID 597653 반응식
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11](O)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].S(Cl)(Cl)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([N:22]=[N+:23]=[N-:24])=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 757754-Acetoxy-3-methoxy-cinnamic acid

생성물 1

HCID 539505664-Acetoxy-3-methoxy-cinnamic acid azide

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

34.0 g (0.145 mol) of 4-acetoxy-3-methoxy-cinnamic acid are suspended in 150 ml of benzene and 21 ml (0.290 mol) of thionyl chloride are added. The mixture is then heated to the boil, under a reflux condenser, for 30 minutes; thereafter, the solvent and excess thionyl chloride are removed by distillation under reduced pressure. The crude 4-acetoxy-3-methoxy-cinnamic acid chloride which remains is dissolved in 150 ml of absolute 1,2-dimethoxyethane, 28.3 g (0.435 mol) of sodium azide are added and the mixture is subsequently stirred for 48 hours at room temperature. The inorganic salts are then filtered off and the filtrate is concentrated under reduced pressure at 30° C, in the course of which colourless crystals separate out. The crystallisation is completed by adding ether. 4-Acetoxy-3-methoxy-cinnamic acid azide of melting point 93°-95° C (decomposition) is obtained.

후처리

  1. temperatureThe mixture is then heated to the boil, under a reflux condenser, for 30 minutes
  2. customthereafter, the solvent and excess thionyl chloride are removed by distillation under reduced pressure
  3. dissolutionThe crude 4-acetoxy-3-methoxy-cinnamic acid chloride which remains is dissolved in 150 ml of absolute 1,2-dimethoxyethane
  4. filtrationThe inorganic salts are then filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure at 30° C, in the course of which colourless crystals
  6. customseparate out
  7. customThe crystallisation
  8. additionby adding ether

출처 및 근거

ORD 기록
ord-037d45bd4547499bbca84d8d119d79d6
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04014920

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