Methanesulfonamide → 5-Chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamide

HRID 512047노트

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HRID 512047 반응식
[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:13][S:14]([NH2:17])(=[O:16])=[O:15].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:17][S:14]([CH3:13])(=[O:16])=[O:15])=[O:8]

참가 물질

6

반응물 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 580424465-Chloro-2-fluoro-4-methylbenzoic acid

생성물 1

HCID 580423685-Chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamide수율 45%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-chloro-2-fluoro-4-methylbenzoic acid (Preparation 21, 200 g, 1.06 mol) in DCM (1.4 L) were added methanesulphonamide (152 g, 1.6 mol), 4-(dimethylamino)pyridine (183 g 1.6 mol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (306 g, 1.6 mol). An exotherm of 30° C. was observed in the first 30 minutes, then the mixture was stirred at room temperature for 18 hours under a nitrogen atmosphere. The reaction mixture was washed with aqueous hydrochloric acid (4 M, 0.8 L). The organic layer was separated, washed with water (500 mL) and dried over sodium sulfate to yield a tan solid, which was recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL) and cooling to afford the title compound (118 g, 45%).

후처리

  1. customAn exotherm of 30° C.
  2. customwas observed in the first 30 minutes
  3. washThe reaction mixture was washed with aqueous hydrochloric acid (4 M, 0.8 L)
  4. customThe organic layer was separated
  5. washwashed with water (500 mL)
  6. dry with materialdried over sodium sulfate
  7. customto yield a tan solid, which
  8. customwas recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL)
  9. temperaturecooling

출처 및 근거

ORD 기록
ord-1966949c10b645d8b589eedfdcda0f2a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102621B2

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