Hydrochloric Acid → HCID 21388795, compound

HRID 1833721Notes

Reaction equation

HRID 1833721 reaction equation
[Na].C(O[CH:5](OCC)[C:6](=[CH:9]O)[C:7]#[N:8])C.Cl.[CH2:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[NH:23])=[CH:20][CH:19]=1)[CH2:16][CH3:17].Cl>O>[C:7]([C:6]1[CH:5]=[N:23][C:22]([C:21]2[CH:25]=[CH:26][C:18]([CH2:15][CH2:16][CH3:17])=[CH:19][CH:20]=2)=[N:24][CH:9]=1)#[N:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 15564092HCID 15564092, compoundHCID 73678895HCID 73678895, compound

Product 1

HCID 21388795HCID 21388795, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

3.26 G. of the crude sodium salt of hydroxymethylene-cyanacetaldehyde diethylacetal are dissolved in 20 ml. of water with stirring. 4.51 G. of p-n-propylbenzamidine hydrochloride are added and the resulting solution, which reacts alkaline, is adjusted to pH 4-5 with 1 ml. of 3-N hydrochloric acid. After stirring for 5 minutes, the mixture is concentrated to dryness at 50° C. in vacuo and the residue is left to stand at room temperature with 50 ml. of acetic anhydride for 16 hours. Then, the mixture is heated to 100° C. for 1 hour, evaporated in vacuo and the residue (brown oil, partly crystalline) is taken up in methylene chloride and chromatographed on silica gel. Elution with methylene chloride and methylene chloride/2% acetone yields 5-cyano-2-(4-n-propylphenyl)-pyrimidine which is recrystallized from acetone/hexane to a constant melting point and then sublimed in a high vacuum at 120° C, whereby there are obtained colorless crystals of said pyrimidine having a melting point of 125.9°-126.0° C, which on cooling are liquid crystalline (monotropic) at 106.4° C.

Workup

  1. customthe resulting solution, which reacts alkaline
  2. concentrationthe mixture is concentrated to dryness at 50° C. in vacuo
  3. waitthe residue is left
  4. customto stand at room temperature with 50 ml
  5. waitof acetic anhydride for 16 hours
  6. customevaporated in vacuo
  7. customchromatographed on silica gel
  8. washElution with methylene chloride and methylene chloride/2% acetone

Sources & evidence

ORD record
ord-df9de3184a984406a5883472b9ae0086
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

Loading…