Cyanamide → HCID 178422937, compound

HRID 1155555Notes

Reaction equation

HRID 1155555 reaction equation
[K].S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:13][C:14]1[CH:19]=[C:18]([C:20](=[N:22]O)[CH3:21])[CH:17]=[CH:16][N:15]=1.[N:24]#[C:25][NH2:26].[OH-].[Na+].[OH-].[NH4+]>CCOCC.C(O)C>[CH3:13][C:14]1[CH:19]=[C:18]([C:20]2[N:22]=[C:25]([NH2:26])[NH:24][CH:21]=2)[CH:17]=[CH:16][N:15]=1

Participants

8

Reactant 5

HCID 9864CyanamideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 5462222PotassiumHCID 136359199HCID 136359199, compound

Product 1

HCID 178422937HCID 178422937, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To 210 mg. of potassium metal dissolved in 10 ml. of absolute ethanol was added a suspension of 1.46 (4.8 mmoles) of 2-methyl-4-acetylpyridine oxime tosylate in 10 ml. of dry ethanol, and the mixture allowed to stir at room temperature for one hour. Ether (200 ml.) was added, the potassium tosylate filtered, and the filtrate extracted with (3×20 ml.) 1 N hydrochloric acid. The combined acid extracts were concentrated to a yellow solid, which was then dissolved in 30 ml. of water. Cyanamide (600 mg., 14.2 mmoles) was dissolved in the aqueous solution and the pH adjusted to 4.5 by the addition of 2 N sodium hydroxide. The solution was heated on a steam bath for one hour, cooled in an ice bath and made basic with concentrated ammonium hydroxide. The mixture was concentrated, and the residue triturated with 15 ml. of ethanol. The solids were filtered and the filtrate was treated with ether. The resulting precipitate was filtered and dried in vacuo, 755 mg. (90%), m.p. 226°-228° C.

Workup

  1. filtrationthe potassium tosylate filtered
  2. extractionthe filtrate extracted with (3×20 ml.) 1 N hydrochloric acid
  3. concentrationThe combined acid extracts were concentrated to a yellow solid, which
  4. dissolutionwas then dissolved in 30 ml
  5. temperatureThe solution was heated on a steam bath for one hour
  6. temperaturecooled in an ice bath
  7. concentrationThe mixture was concentrated
  8. customthe residue triturated with 15 ml
  9. filtrationThe solids were filtered
  10. additionthe filtrate was treated with ether
  11. filtrationThe resulting precipitate was filtered
  12. customdried in vacuo, 755 mg

Sources & evidence

ORD record
ord-db63fe03cc794a5396c07d30d60a8853
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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