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

HRID 508423노트

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HRID 508423 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

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온도
30 °C

실험 절차

To 5-chloro-2-fluoro-4-methylbenzoic acid (Preparation 13, 200 g, 1.06 mol) in DCM (1.4 L) was 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). The reaction mixture spontaneously heated at 30° C. over 30 minutes, then it was stirred at room temperature for 18 hours under a nitrogen atmosphere. The reaction was washed with aqueous hydrochloric acid (4 M, 0.8 L). The organic layer was separated, washed with water (500 mL), dried over sodium sulphate and concentrated in vacuo to yield a tan solid, which was recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL) and cooling to yield the title compound (118 g, 45%).

후처리

  1. washThe reaction was washed with aqueous hydrochloric acid (4 M, 0.8 L)
  2. customThe organic layer was separated
  3. washwashed with water (500 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customto yield a tan solid, which
  7. customwas recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL)
  8. temperaturecooling

출처 및 근거

ORD 기록
ord-f859e0a88e5f450c9d532179c46ae236
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096500B2

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