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

HRID 1380046Notes

Reaction equation

HRID 1380046 reaction equation
[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]

Participants

10

Reactant 6

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

Product 1

HCID 135903993-Cyano-N,N-dimethylbenzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a731acfb479b4a9b8a500eda84ca313e
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

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