Dimethylformamide → HCID 66911330, 화합물

HRID 340659

반응식

HRID 340659 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=O)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)(Cl)=O.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[SH:36]>C(Cl)Cl.N1C=CC=CC=1.O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[S:36][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[N:29]=2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 87132-AminothiophenolHCID 24386Thionyl ChlorideHCID 2263354-(Benzyloxy)-3-methoxybenzoic acid

생성물 1

HCID 66911330HCID 66911330, 화합물

시약·촉매·용매 4

HCID 962Water용매2회HCID 1049Pyridine용매HCID 1140Toluene용매2회HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

In methylene chloride (10 ml) was suspended 2.0 g (7.7 mmol) of 4-benzyloxy-3-methoxy benzoic acid. To this suspension was added 0.05 g of DMF and 0.68 ml of thionyl chloride, followed by stirring at 50° C. for 2 hours. This reaction solution was introduced dropwise at 0° C. into a solution wherein 1.2 g (9.3 mmol) of 2-aminothiophenol had been dissolved in 10 ml of pyridine at room temperature. The mixture was further stirred overnight at room temperature, diluted with water, and subjected to ethyl acetate extraction (50 ml×2 times). The extracts were dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue thus obtained was dissolved in 30 ml of toluene. This toluene solution was heated to reflux overnight while water was distilled off. Toluene was removed from this solution by distillation under reduced pressure, and the residue was purified using a silica gel column (eluant:ethyl acetate/hexane=1/5). The solvent was distilled off under reduced pressure. Using the crystals thus obtained, the desired compound was recrystallized in an amount of 0.18 g from methylene chloride-hexane.

후처리

  1. waitThe mixture was further stirred overnight at room temperature
  2. extractionsubjected to ethyl acetate extraction (50 ml×2 times)
  3. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue thus obtained
  6. distillationwas distilled off
  7. customToluene was removed from this solution by distillation under reduced pressure
  8. customthe residue was purified
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthus obtained
  11. customthe desired compound was recrystallized in an amount of 0.18 g from methylene chloride-hexane

출처 및 근거

ORD 기록
ord-601a2c7cf5f540bf80d41a7047f198a8
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895599B2

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