2-Fluoroaniline → 2-Fluoro-4-thiocyanatoaniline

HRID 605421

反応式

HRID 605421 の反応式
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[S-:9][C:10]#[N:11].[Na+].BrBr.C([O-])(O)=O.[Na+]>CO.[Na+].[Br-].CO.O>[F:1][C:2]1[CH:8]=[C:7]([S:9][C:10]#[N:11])[CH:6]=[CH:5][C:3]=1[NH2:4]

参加物

8

反応物 4

HCID 95842-FluoroanilineHCID 24408BromineHCID 516871Sodium thiocyanateHCID 516892Sodium Bicarbonate

生成物 1

HCID 43563652-Fluoro-4-thiocyanatoaniline収率 86.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 20267117Sodium bromide methanol溶媒

実験手順

2-Fluoroaniline (9.8 mL, 0.1 mol) and sodium thiocyanate (24.9 g, 0.3 mol) in MeOH (55 mL) were treated with a cold solution of bromine (5.7 mL, 0.11 mol) in saturated NaBr-MeOH solution (50 mL) added dropwise at −5-0° C. over 2 hours. After the addition, the reaction mixture was poured into cold water (200 mL) with stirring, adjusted to pH 8-9 with NaHCO3 (10 g), and stirred at 5° C. for 30 minutes. The resulting crystals were collected by filtration, washed with cold water, and dried at room temperature overnight in vacuum to give crude product 2-fluoro-4-thiocyanatoaniline (14.5 g) as slightly brown crystal. A mixture of the crude 2-fluoro-4-thiocyanatoaniline (14.5 g) and concentrated hydrochloric acid (58 mL) in EtOH (15 mL) was refluxed for 8 hours. The reaction mixture was cooled and stirred at room temperature overnight. The resulting crystals were collected by filtration, washed with cold EtOH and i-Pr2O, dried at room temperature overnight in vacuum to give the title compound as its hydrochloride salt (pale yellow crystal, 10.1 g, 56%).

後処理

  1. additionadded dropwise at −5-0° C. over 2 hours
  2. additionAfter the addition
  3. stirringstirred at 5° C. for 30 minutes
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with cold water
  6. customdried at room temperature overnight in vacuum

出典と根拠

ORDレコード
ord-c24c06d0fcf942ecb7625a9a994ae638
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

関連ノート

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