Dimethylformamide → HCID 20393375, compound

HRID 1863084Notes

Reaction equation

HRID 1863084 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].CN(C)C=O.C([Li])CCC.C([O:21][C:22]([C:24]1[N:25]([CH3:40])[C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:27]2[C:32]=1[CH:31]=[CH:30][C:29]([Cl:33])=[CH:28]2)=O)C>CCCCCC>[ClH:33].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:22]([C:24]1[N:25]([CH3:40])[C:26]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[C:27]2[C:32]=1[CH:31]=[CH:30][C:29]([Cl:33])=[CH:28]2)=[O:21])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 60993N,N-DiethylethylenediamineHCID 54012509Ethyl 5-chloro-2-methyl-3-phenyl-2H-isoindole-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 20393375HCID 20393375, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2.3 g. of 2-diethylaminoethylamine in 25 ml. of dimethylformamide is treated under an atmosphere of argon at 5°-10° C. with 0.02 mol. of butyllithium (10 ml. of a 2-M solution in hexane). Then, there is added at 20°-25° C. a solution of 3.2 g of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid ethyl ester in 15 ml. of dimethylformamide, the hexane is removed by distillation and the mixture is subsequently stirred at 120° C. for 1 hour. After cooling, the mixture is poured on to 200 ml. of ice-water, the separated oil extracted with methylene chloride and the extract washed with water and evaporated to dryness. The residue is dissolved in 100 ml. of diethyl ether and the solution obtained extracted with 0.5-N hydrochloric acid. The ethereal phase contains unreacted starting material which can be recovered after concentration of the solution. The aqueous acid extract is made alkaline with concentrated ammonia solution at 0°- 5° C. and the separated oil extracted with diethyl ether. The ethereal extract is washed with water, dried over sodium sulfate and concentrated to dryness. The residual base is dissolved in 5 ml. of acetone and treated with excess ethereal hydrochloric acid. The hydrochloride which crystallizes out is removed by filtration and washed with diethyl ether, and there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [2-(diethylamino)ethyl]amide hydrochloride having a melting point of 211°-214° C. (decomposition).

Workup

  1. customof dimethylformamide, the hexane is removed by distillation
  2. temperatureAfter cooling
  3. additionthe mixture is poured on to 200 ml
  4. extractionof ice-water, the separated oil extracted with methylene chloride
  5. washthe extract washed with water
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved in 100 ml
  8. customof diethyl ether and the solution obtained
  9. extractionextracted with 0.5-N hydrochloric acid
  10. customcan be recovered after concentration of the solution
  11. extractionThe aqueous acid extract
  12. customat 0°- 5° C.
  13. extractionthe separated oil extracted with diethyl ether
  14. extractionThe ethereal extract
  15. washis washed with water
  16. dry with materialdried over sodium sulfate
  17. concentrationconcentrated to dryness
  18. dissolutionThe residual base is dissolved in 5 ml
  19. additionof acetone and treated with excess ethereal hydrochloric acid
  20. customThe hydrochloride which crystallizes out
  21. customis removed by filtration
  22. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2b745feb550e40a19687ec339baa0e98
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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