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Barbituric Acid → Ethylenediamine

HRID 128358
Notes
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Reaction equation

HRID 128358 reaction equation
C1C=C2C(N)=NC(=N)C2=CC=1.[C:12]([CH2:14][C:15]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:25])[CH2:22][C:23]#[N:24])=[O:16])#[N:13].[NH:26]1[C:33](=O)[CH2:32][C:30](=[O:31])NC1=O.C1C(=NNC2C=CC(/C=C/C3C=CC(NN=C4C=CC(=O)C=C4)=CC=3S([O-])(=O)=O)=C(S([O-])(=O)=O)C=2)C=C[C:37](=[O:38])[CH:36]=1.[Na+].[Na+]>O.C(O)(=O)C>[C:23]([CH2:22][C:21]([NH:20][CH2:19][CH2:18][NH:17][C:15](=[O:16])[CH2:14][C:12]#[N:13])=[O:25])#[N:24].[CH2:19]([NH2:20])[CH2:18][NH2:17].[C:33]([CH2:32][C:30]([O:38][CH2:37][CH3:36])=[O:31])#[N:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6211Barbituric AcidHCID 189801H-Isoindol-3-amine, 1-imino-HCID 76682N,N'-Ethylenebis(2-cyanoacetamide)HCID 178516258HCID 178516258, compound

Product 3

HCID 3301EthylenediamineHCID 7764Ethyl cyanoacetate
HCID 76682
N,N'-Ethylenebis(2-cyanoacetamide)

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3.87 g of 1-amino-3-imino-isoindolenine and 1.95 g of bis-cyanoacetylethylenediamine are heated in 50 ml of water for 2 hours to reflux temperature. Then 2.56 g of barbituric acid and 20 ml of acetic acid are added and the mixture is refluxed for a further 5 hours. The pigment is collected hot with suction and washed with water and dried, affording 5.1 g of a yellow colourant powder. When incorporated in lacquers without further treatment, this pigment produces brilliant, strong colourations of outstanding fastness to overstripe bleeding. For incorporation in printing inks or plastics, the pigment is advantageously brought into the form of a preparation. This is accomplished by known methods by coating the finely dispersed pigment with substrate-compatible resins. When the pigment is used in printing, brilliant yellow colourations of excellent lightfastness are obtained. The bis-cyanoacetylethylenediamine (m.p. 191° C.) is obtained by conventional methods by reaction of ethylenediamine with ethyl cyanoacetate.

Workup

  1. temperatureto reflux temperature
  2. temperaturethe mixture is refluxed for a further 5 hours
  3. customThe pigment is collected hot with suction
  4. washwashed with water
  5. customdried
  6. customaffording 5.1 g of a yellow colourant powder
  7. customthis pigment produces brilliant
  8. customthe pigment is advantageously brought into the form of a preparation
  9. customare obtained

Sources & evidence

ORD record
ord-ecf5468935cf4ef5bb8fd07f3c8d4f85
Source dataset
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04259488

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes