Hydrochloric Acid → HCID 178517653, compound

HRID 1707038Notes

Reaction equation

HRID 1707038 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:10]C=O)=N)=[CH:4][CH:3]=1.[NH2:13][C:14]([NH2:16])=[O:15].Cl.[CH2:18](O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:10]=[N:13][C:14]([OH:15])=[N:16][CH:18]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702Ethanol2×HCID 1176UreaHCID 86737069HCID 86737069, compound

Product 1

HCID 178517653HCID 178517653, compound

Procedure

A mixture of 20.0 g. of (p-chlorophenyl)formimidoylacetaldehyde and 5.0 g. of urea is heated under reflux in 50 ml. of ethanol and 10 ml. of concentrated hydrochloric acid for 5 hours. The reaction mixture is worked up as described in Example 4 and the product is crystallized from ethanol to give 13.0 g. of a solid. The solid in 260 ml. of ethanol and 13 ml. of concentrated hydrochloric acid is heated under reflux for 16 hours. The reaction mixture is cooled and the material which is separated is collected and dissolved in a minimum of dimethyl sulfoxide. Dilute ammonium hydroxide (20%) is added and the product is collected, washed with water, ethanol, and ether to yield 8.78 g. of the product of the Example, m.p. 324°-327° C.

Workup

  1. additionA mixture of 20.0 g
  2. temperatureunder reflux in 50 ml
  3. customthe product is crystallized from ethanol
  4. customto give 13.0 g
  5. temperatureunder reflux for 16 hours
  6. temperatureThe reaction mixture is cooled
  7. customthe material which is separated
  8. customis collected
  9. dissolutiondissolved in a minimum of dimethyl sulfoxide
  10. additionDilute ammonium hydroxide (20%) is added
  11. customthe product is collected
  12. washwashed with water, ethanol, and ether
  13. customto yield 8.78 g

Sources & evidence

ORD record
ord-48482ad7ffd043788dfd8275aec43310
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Reaction notes

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