Ethylenediamine → HCID 15564119, compound

HRID 1105660Notes

Reaction equation

HRID 1105660 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 at 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% aqueous ethylenediamine solution are added and, after stirring for a short time, the mixture is extracted with methylene chloride. The organic extract is shaken with a further 25 ml. of ethylenediamine solution and then washed until neutral. The crude concentrate is chromatographed on silica gel with toluene/1% acetone. Recrystallization of the pure fractions from ethyl acetate yields 5-n-pentyl-2-(4'-cyano-4-biphenylyl)-pyrimidine, having a melting point of 123.5°-124° C. and clearing point of 204.5°-205° C.

Workup

  1. temperatureat reflux 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 with a further 25 ml
  6. washof ethylenediamine solution and then washed until neutral
  7. concentrationThe crude concentrate
  8. customis chromatographed on silica gel with toluene/1% acetone
  9. customRecrystallization of the pure fractions from ethyl acetate

Sources & evidence

ORD record
ord-571cbe0dadca4bf9a1061156b82d97d7
Source dataset
uspto-grants-1982_01
Patent number
US04309539

Reaction notes

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