Sodium Cyanide → HCID 131711729, compound

HRID 2049119Notes

Reaction equation

HRID 2049119 reaction equation
N[C:2]1C(C(OC)=[O:11])=NC(I)=C(N)N=1.[C-]#N.[Na+].O.[NH2:18][C:19]1[C:20]([C:28]([OH:30])=[O:29])=[N:21][C:22]([C:26]#[N:27])=[C:23]([NH2:25])[N:24]=1.[NH2:31][C:32]1[C:33]([C:41]([OH:43])=[O:42])=[N:34][C:35]([C:39]#[N:40])=[C:36]([NH2:38])[N:37]=1>CN(C)P(N(C)C)(N(C)C)=O>[OH2:11].[NH2:18][C:19]1[C:20]([C:28]([O:30][CH3:2])=[O:29])=[N:21][C:22]([C:26]#[N:27])=[C:23]([NH2:25])[N:24]=1.[CH3:2][O:42][C:41]([C:33]1[C:32]([NH2:31])=[N:37][C:36]([NH2:38])=[C:35]([C:39]#[N:40])[N:34]=1)=[O:43]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 15148127HCID 15148127, compoundHCID 131711730HCID 131711730, compound

Product 1

HCID 131711729HCID 131711729, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 3,5-diamino-6-iodo-2-pyrazinoate (370 mg., 0.0012 mole), cuprous cyanide (215 mg., 0.0024 mole) and hexamethylphosphoramide (10 ml.) are combined and heated at 100° C. for 15 minutes. After cooling to 25° C. the reaction mixture is added to aqueous sodium cyanide solution, stirred at 25° C. for 1 hour and extracted with CHCl3. The CHCl3 layer was washed with dilute NaCN solution, then with H2O, and dried (MgSO4). After evaporation of the CHCl3, the residual oil was treated with hexane to give 75 mg. of methyl, 3,5-diamino-6-cyano-2-pyrazinoate hemihydrate melting at 284°-5° C.

Workup

  1. temperatureAfter cooling to 25° C. the reaction mixture
  2. extractionextracted with CHCl3
  3. washThe CHCl3 layer was washed with dilute NaCN solution
  4. dry with materialwith H2O, and dried (MgSO4)
  5. customAfter evaporation of the CHCl3
  6. additionthe residual oil was treated with hexane
  7. customto give 75 mg

Sources & evidence

ORD record
ord-9f87dfee7f664a53aff9805036f3c92e
Source dataset
uspto-grants-1980_04
Patent number
US04196292

Reaction notes

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