Hydrochloric Acid → 3-Cyano-N,N-dimethylbenzamide

HRID 1380046ノート

反応式

HRID 1380046 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])#[N:2].S(Cl)(Cl)=O.S(=O)=O.Cl.[CH2:20]([NH:22][CH2:23]C)C.[OH-].[K+]>O.CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([N:22]([CH3:23])[CH3:20])=[O:7])#[N:2]

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 8021DiethylamineHCID 14797Potassium HydroxideHCID 158753-Cyanobenzoic acidHCID 24386Thionyl Chloride

生成物 1

HCID 135903993-Cyano-N,N-dimethylbenzamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 85.22 g of m-cyanobenzoic acid, 400 ml of toluene, 4.48 ml (4.23 g) of N,N-dimethylformamide and 44.4 ml (72.3 g) of thionyl chloride was gently heated on a steam bath for 2 hours with sulfur dioxide and hydrogen chloride being evolved. The reaction solution was cooled in an ice bath and cautiously added portionwise, over one hour, to stirred and cooled solution of 250 ml of 40% aqueous diethylamine and 100 ml of water. At intervals 2-3 ml of concentrated aqueous potassium hydroxide was added. After the addition was complete, the mixture was stirred for several hours, then the layers were separated and the organic layer washed with water. After permitting the organic layer to evaporate to dryness, the residue was recrystallized from 300 ml of ethanol containing charcoal, giving 68.5 g of the desired compound as white crystals, mp 85°-88° C.

後処理

  1. temperatureThe reaction solution was cooled in an ice bath
  2. additioncautiously added portionwise, over one hour
  3. additionAfter the addition
  4. stirringthe mixture was stirred for several hours
  5. customthe layers were separated
  6. washthe organic layer washed with water
  7. customto evaporate to dryness
  8. customthe residue was recrystallized from 300 ml of ethanol
  9. additioncontaining charcoal

出典と根拠

ORDレコード
ord-a731acfb479b4a9b8a500eda84ca313e
出典データセット
uspto-grants-1986_04
特許番号
US04579848

反応ノート

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