Ethyl chloroformate → HCID 178473542, compound

HRID 1706681Notes

Reaction equation

HRID 1706681 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])[NH2:2].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>N1C=CC=CC=1>[NH2:13][C:12]1[C:7]([C:5]([N:4]=[C:1]([NH:2][C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:3][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:6])=[N:8][C:9]([Cl:15])=[C:10]([NH2:14])[N:11]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 178513083HCID 178513083, compound

Product 1

HCID 178473542HCID 178473542, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred suspension of N-amidino-3,5-diamino-6-chloro-2-pyrazinecarboxamide (27.6 g., 0.12 mole) in pyridine (300 ml.) is added ethyl chloroformate (12.0 ml., 0.15 mole) during a 5 minute period. The reaction is stirred at 25° for 2 hours during which time the starting material dissolves and the hydrochloride of the starting material precipitates. The latter is filtered from the reaction and discarded. The filtrate is treated with water (700 ml.) to give 16 g. (71%) of 3,5-diamino-6-chloro-N-[bis(ethoxycarbonylamino)methylene]-2-pyrazinecarboxamide which melts at 213° C. after recrystallization from ethanol.

Workup

  1. dissolutiondissolves
  2. customthe hydrochloride of the starting material precipitates
  3. filtrationThe latter is filtered from the reaction
  4. additionThe filtrate is treated with water (700 ml.)
  5. customto give 16 g
  6. custom(71%) of 3,5-diamino-6-chloro-N-[bis(ethoxycarbonylamino)methylene]-2-pyrazinecarboxamide which melts at 213° C. after recrystallization from ethanol

Sources & evidence

ORD record
ord-e04025a0269c4e9b920918f0016f0a49
Source dataset
uspto-grants-1980_06
Patent number
US04208413

Reaction notes

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