Sodium Bicarbonate → N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamide

HRID 1662222

反応式

HRID 1662222 の反応式
[Cl:1][C:2]1[CH:9]=[C:8]([C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:5]([C:6]#[N:7])=[C:4]([F:20])[CH:3]=1.[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([C:6]#[N:7])=[C:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:27][S:25]([C:22]([CH3:24])([CH3:23])[CH3:21])=[O:26])[CH:9]=1

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 585795244-Chloro-2-fluoro-6-(3-methoxybenzoyl)benzonitrile

生成物 1

HCID 76821604N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamide収率 59%

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

4-Chloro-2-fluoro-6-(3-methoxybenzoyl)benzonitrile (2.56 g, 8.84 mmol), 2-methyl-2-propanesulfinamide (1.392 g, 11.49 mmol) and titanium(IV) ethoxide (4.62 mL, 22.09 mmol) were dissolved in THF (30 mL) and stirred at 75° C. over weekend. When cooled to rt, the mixture was diluted with DCM (25 mL). Saturated aqueous NaHCO3 (3 mL) was added followed by silica and the mixture concentrated under reduced pressure until a free flowing powder was obtained. Purification on a silica gel column (0-40% EtOAc in heptane as eluent) gave 2.04 g (59% yield) of the title compound.

後処理

  1. temperatureWhen cooled to rt
  2. concentrationthe mixture concentrated under reduced pressure until
  3. customwas obtained
  4. customPurification on a silica gel column (0-40% EtOAc in heptane as eluent)

出典と根拠

ORDレコード
ord-751b48230fcf4f98beb5a0f168bc0b32
出典データセット
uspto-grants-2011_10
特許番号
US08030500B2

関連ノート

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