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

HRID 508423ノート

反応式

HRID 508423 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

反応条件

温度
30 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f859e0a88e5f450c9d532179c46ae236
出典データセット
uspto-grants-2015_08
特許番号
US09096500B2

反応ノート

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