Dimethylformamide → HCID 178465363, compound

HRID 2083366Notes

Reaction equation

HRID 2083366 reaction equation
[C:1]([NH:4][C:5]([C:7]1[C:12]([NH2:13])=[N:11][C:10]([NH2:14])=[C:9]([Cl:15])[N:8]=1)=[O:6])(=[NH:3])N.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17].C[N:22](C)C=O>>[OH2:6].[ClH:15].[NH2:13][C:12]1[C:7]([C:5]([N:4]=[CH:1][NH:3][NH:22][C:19]([NH:18][CH2:16][CH3:17])=[O:20])=[O:6])=[N:8][C:9]([Cl:15])=[C:10]([NH2:14])[N:11]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8022Ethyl isocyanateHCID 178513083HCID 178513083, compound

Product 1

HCID 178465363HCID 178465363, compound

Conditions

Temperature
90 °C

Procedure

N-Amidino-3,5-diamino-6-chloro-2-pyrazinecarboxamide (9.16 g., 0.04 mole) dissolved in N,N-dimethylformamide (240 ml.) is treated dropwise with ethyl isocyanate (3.16 g., 0.044 mole) over a 10 minute period at 90° C. and heated at 90° C. for 3 hours. The reaction mixture is filtered and poured into water (1 1.) to precipitate 3,5-diamino-6-chloro-N-{[ (ethylaminocarbonyl)amino]aminomethylene}-2-pyrazinecarboxamide. The hydrochloride monohydrate (6.80 g.) is obtained on crystallization from abs. ethanol (800 ml.) and treatment of the hot solution with 12N hydrochloric acid (5 ml.), m.p. 224°-255° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. additionpoured into water (1 1.)
  3. customto precipitate 3,5-diamino-6-chloro-N-{[ (ethylaminocarbonyl)amino]aminomethylene}-2-pyrazinecarboxamide

Sources & evidence

ORD record
ord-4ee4d9114afd49f6a371e89ded5997eb
Source dataset
uspto-grants-1978_04
Patent number
US04085211

Reaction notes

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