Hydrochloric Acid → N-(4-Pyridinylmethyl)urea

HRID 2305381Notes

Reaction equation

HRID 2305381 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[O-:10][C:11]#[N:12].[Na+].[O-]C#N>O>[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:11]([NH2:12])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 773174-PyridinemethanamineHCID 517096Sodium CyanateHCID 178513472HCID 178513472, compound

Product 1

HCID 13227714N-(4-Pyridinylmethyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.1 ml of 5N HCl was added to a solution of 2.53 ml of 4-picolylamine and 1.66 g of sodium cyanate in 50 ml of water. After 5 hours, a further 0.166 g of cyanate were added and the pH adjusted to 7.5. After 18 hours the reaction mixture was evaporated to dryness, the residue extracted with 100 ml of hot 2-propanol. The filtrate was concentrated, cooled and the solid collected to give the title compound (3.03 g) mp 194-6° C. A further 0.63 g could be isolated as second and third crops.

Workup

  1. customAfter 18 hours the reaction mixture was evaporated to dryness
  2. extractionthe residue extracted with 100 ml of hot 2-propanol
  3. concentrationThe filtrate was concentrated
  4. temperaturecooled
  5. customthe solid collected

Sources & evidence

ORD record
ord-164fe147d2c4411fa9f9cae64beefb80
Source dataset
uspto-grants-2002_08
Patent number
US06440979B1

Reaction notes

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