Dimethylformamide → HCID 68578370, 화합물

HRID 886975노트

반응식

HRID 886975 반응식
[Br:1][C:2]1[C:3]([F:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.[CH3:13][N:14]([CH3:17])C=O.[C:18](Cl)(=[O:22])C(Cl)=O>C1(C)C=CC=CC=1>[CH2:17]([N:14]([CH2:13][CH2:18][OH:22])[C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]([Br:1])[C:3]=1[F:12])[C:2]1[CH:3]=[CH:4][CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 111490783-BROMO-2,4-DIFLUOROBENZOIC ACID

생성물 1

HCID 68578370HCID 68578370, 화합물수율 90.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of 3-bromo-2,4-difluorobenzoic acid (1.00 g, 4.22 mmol), N,N-dimethylformamide (0.2 ml) and toluene (20 ml) was added under ice-cooling oxalyl dichloride (0.434 ml). The mixture was stirred at room temperature for 1 hr, and the solvent was evaporated under reduced pressure. To a solution of the residue in tetrahydrofuran (30 ml) were added N-benzylethanolamine (702 mg) and 1N aqueous sodium hydroxide solution (10 ml), and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (1.41 g, 90.3%) as a solid.

후처리

  1. additionwas added under ice-
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo a solution of the residue in tetrahydrofuran (30 ml) were added N-benzylethanolamine (702 mg) and 1N aqueous sodium hydroxide solution (10 ml)
  4. stirringthe mixture was stirred at room temperature for 0.5 hr
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washThe extract was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-fee1ab5e8c82486294b8d8d2c48a03ba
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247403B2

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