Dimethylformamide → HCID 54488893, compound

HRID 1863083Notes

Reaction equation

HRID 1863083 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:22])[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=O)C.C[N:24](C)C=O.[NH2-].[Na+]>C1(C)C=CC=CC=1>[Cl:15][C:11]1[CH:12]=[CH:13][C:14]2[C:9](=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:7]([CH3:22])[C:6]=2[C:4]([NH2:24])=[O:3])[CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24533Sodium amideHCID 54012509Ethyl 5-chloro-2-methyl-3-phenyl-2H-isoindole-1-carboxylate

Product 1

HCID 54488893HCID 54488893, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 12.4 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid ethyl ester in 70 ml. of dimethylformamide is treated under an atmosphere of argon at room temperature with 0.1 mol. of sodium amide (8.0 g. of a 50% suspension in toluene) and then stirred at 100° C. for 2 hours. After cooling, the mixture is poured on to 400 ml. of ice-water and the precipitate is removed by filtration, washed with water and dissolved in methylene chloride. The organic solution is washed with water, dried over sodium sulfate and concentrated to dryness. The residue is dissolved in chloroform and chromatographed on 800 g. of silica gel using chloroform/n-heptane/ethanol (10:10:1) for the elution. The uniform fractions are combined and evaporated. After recrystallization from acetonitrile, there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid amide in the form of yellowish crystals having a melting point of 241°-244° C. (decomposition).

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured on to 400 ml
  3. customof ice-water and the precipitate is removed by filtration
  4. washwashed with water
  5. dissolutiondissolved in methylene chloride
  6. washThe organic solution is washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness
  9. dissolutionThe residue is dissolved in chloroform
  10. customchromatographed on 800 g
  11. washfor the elution
  12. customevaporated
  13. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-451c3b7323634315a3234b8d60b5fb56
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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