Dimethylformamide → HCID 178508801, compound

HRID 261016Notes

Reaction equation

HRID 261016 reaction equation
C([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])(=N)N.C1C[N:23]2[C:18](=[N:19]CCC2)C1.[CH2:25]([O:32][P:33](Cl)[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CN(C)C=[O:46]>>[NH2:13][C:12]1[C:7]([C:5]([NH:4][N:19]=[CH:18][NH:23][P:33](=[O:46])([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:6])=[N:8][C:9]([Cl:15])=[C:10]([NH2:14])[N:11]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 4372071DibenzylchlorophosphiteHCID 178513083HCID 178513083, compound

Product 1

HCID 178508801HCID 178508801, compound

Conditions

Temperature
25 °C

Procedure

A stirred solution of N-amidino-3,5-diamino-6-chloropyrazinamide (4.6 g., 0.02 mole) and DBN (2.5 g., 0.02 mole) in dimethylformamide (150 ml) is treated with dibenzylchlorophosphite (6.6 g., 0.22 mole) in one portion. The reaction mixture is stirred at 25° C. for 18 hours, filtered and treated with water to precipitate dibenzyl N-[3,5-diamino-6-chloro-pyrazinamido)iminomethyl]phosphoramidate which melts at 187° C.

Workup

  1. filtrationfiltered
  2. additiontreated with water
  3. customto precipitate dibenzyl N-[3,5-diamino-6-chloro-pyrazinamido)iminomethyl]phosphoramidate which melts at 187° C.

Sources & evidence

ORD record
ord-313d18eb495148c48f658f4aa9eb3574
Source dataset
uspto-grants-1979_08
Patent number
US04163781

Reaction notes

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