Dimethylformamide → HCID 178457959, compound

HRID 2083367Notes

Reaction equation

HRID 2083367 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:19]=[C:20]=[O:21])[CH2:17][CH3:18].C[N:23](C)C=O>>[NH2:13][C:12]1[C:7]([C:5]([N:4]=[CH:1][NH:3][NH:23][C:20]([NH:19][CH2:16][CH2:17][CH3:18])=[O:21])=[O:6])=[N:8][C:9]([Cl:15])=[C:10]([NH2:14])[N:11]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 61033Propyl isocyanateHCID 178513083HCID 178513083, compound

Product 1

HCID 178457959HCID 178457959, compound

Conditions

Temperature
90 °C

Procedure

N-amidino-3,5-diamino-6-chloro-2-pyrazinecarboxamide (4.58 g., 0.02 mole) dissolved in N,N-dimethylformamide (120 ml.) is treated dropwise with propylisocyanate (1.87 g., 0.022 mole) over a 10 min. period at 90° C. The solution is heated at 90° C. for 1 hour, filtered and poured into water (150 ml.) to precipitate 3,5-diamino-6-chloro-N-{[ (propylaminocarbonyl)amino]aminomethyl-}-2-pyrazinecarboxamide which on recrystallization from n-propanol gives 3.14 g. melting at 220°-221° C.

Workup

  1. filtrationfiltered
  2. additionpoured into water (150 ml.)
  3. customto precipitate 3,5-diamino-6-chloro-N-{[ (propylaminocarbonyl)amino]aminomethyl-}-2-pyrazinecarboxamide which
  4. customon recrystallization from n-propanol
  5. customgives 3.14 g

Sources & evidence

ORD record
ord-f6c07b4e7d714b03a5acd45185e2e69e
Source dataset
uspto-grants-1978_04
Patent number
US04085211

Reaction notes

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