Dimethyl Sulfate → Methyl 3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)-5-nitrobenzoate

HRID 1373194노트

반응식

HRID 1373194 반응식
[F:1][C:2]1[C:3]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[F:11])[C:5]([OH:7])=[O:6].[C:24](=O)(O)[O-].[Na+].COS(OC)(=O)=O.CCCCCC>CC(C)=O.CCOC(C)=O>[CH3:24][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]([F:11])=[C:2]([F:1])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23]

참가 물질

7

반응물 4

HCID 6497Dimethyl SulfateHCID 8058HexaneHCID 516892Sodium BicarbonateHCID 210742923,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoic acid

생성물 1

HCID 58781115Methyl 3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)-5-nitrobenzoate

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-nitro-benzoic acid (595.3 g, 1.363 mol) in acetone (9 L) was added sodium bicarbonate (609.0 g, 3.48 mol) and the mixture was stirred for 10 min. To this suspension was added dimethylsulfate (285.6 ml, 3.026 mol) and refluxed for 3 h (completion of reaction was confirmed by TLC-hexane: EtOAc/4:1), cooled to room temperature and evaporated under vacuum. The residue (yellow) was further digested in hot methanol (2 L), filtered, washed with methanol and dried to give the title compound as a solid (yellow). Yield: 405.63g (65.54%).

후처리

  1. temperaturerefluxed for 3 h
  2. customevaporated under vacuum
  3. filtrationfiltered
  4. washwashed with methanol
  5. customdried

출처 및 근거

ORD 기록
ord-558c4bb42bc54c82a1524ebc74602d7d
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160915B2

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