Ethylenediamine → HCID 15564119, compound

HRID 461304Notes

Reaction equation

HRID 461304 reaction equation
[CH2:1]([C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cu][C:26]#[N:27].C(N)CN>CN(C)C=O>[CH2:1]([C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:26]#[N:27])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[N:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 15564114HCID 15564114, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 15564119HCID 15564119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g. of 5-n-pentyl-2-(4'-bromo-4-biphenylyl)-pyrimidine are heated to the reflux for 22 hours with 2.5 g. of copper-(I) cyanide (content 70%) in 50 ml. of dimethylformamide. After cooling, 25 ml. of 10% strength aqueous ethylenediamine solution are added and, after stirring for a short time, the mixture is extracted with methylene chloride. The organic extract is shaken again with 25 ml. of ethylenediamine solution and then washed until it gives a neutral reaction. The crude concentrate is chromatographed with toluene/1% acetone on silica gel. Recrystallization of the pure fractions from ethyl acetate gives 5-n-pentyl-2-(4'-cyano-4-biphenylyl)-pyrimidine, m.p. 123.5°-124°; cl.p. 204.5°-205°.

Workup

  1. temperaturereflux for 22 hours with 2.5 g
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with methylene chloride
  4. extractionThe organic extract
  5. stirringis shaken again with 25 ml
  6. washof ethylenediamine solution and then washed until it
  7. customgives
  8. customa neutral reaction
  9. concentrationThe crude concentrate
  10. customis chromatographed with toluene/1% acetone on silica gel
  11. customRecrystallization of the pure fractions from ethyl acetate

Sources & evidence

ORD record
ord-f39da54875914ae0a2f5a2e041fe7046
Source dataset
uspto-grants-1977_12
Patent number
US04062798

Reaction notes

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