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

HRID 512047ノート

反応式

HRID 512047 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1966949c10b645d8b589eedfdcda0f2a
出典データセット
uspto-grants-2015_08
特許番号
US09102621B2

反応ノート

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