Dimethylformamide → 5-Chloro-2,4-dinitrobenzamide

HRID 2288019ノート

反応式

HRID 2288019 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Cl:16])=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].C[N:18](C=O)C.[OH-].[NH4+]>S(Cl)(Cl)=O.CC(C)=O>[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Cl:16])=[CH:9][C:5]=1[C:6]([NH2:18])=[O:7])([O-:3])=[O:2]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 37278605-Chloro-2,4-dinitrobenzoic acid

生成物 1

HCID 148972315-Chloro-2,4-dinitrobenzamide収率 84%

試薬・触媒・溶媒 2

HCID 24386Thionyl Chloride触媒HCID 180Acetone溶媒

実験手順

2,4-Dinitro-5-chlorobenzoic acid (7.00 g, 28.4 mmol) was suspended in 40 mL thionyl chloride containing 3 drops of DMF. The suspension was warmed to reflux for four hours. After cooling to room temperature, solvent was removed by rotary evaporation leaving a golden yellow liquid. This was diluted with 30 mL acetone and added dropwise over 20 minutes to a 0° C. solution of 20 mL concentrated ammonium hydroxide. The reaction was stirred at 0° C. for 30 minutes, then poured into 250 g of ice. The yellow orange precipitate was collected by filtration and washed well with water. The solid was dried first by water aspirator then under high vacuum to furnish 5.9 g (24 mmol, 84% yield) of product. NMR (400 MHz; acetone-d6): δ 8.75, s 1H, 8.25, s 1H; mp 201-203° C.

後処理

  1. temperatureThe suspension was warmed
  2. temperatureto reflux for four hours
  3. customsolvent was removed by rotary evaporation
  4. customleaving a golden yellow liquid
  5. filtrationThe yellow orange precipitate was collected by filtration
  6. washwashed well with water
  7. dry with materialThe solid was dried first by water aspirator then under high vacuum

出典と根拠

ORDレコード
ord-cb1a0236540d47a7867bff0c669ea6a6
出典データセット
uspto-grants-2000_07
特許番号
US06087368

反応ノート

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