Dimethylformamide → HCID 178476927, compound

HRID 261015

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.[P:25](Cl)([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28].CN(C)C=[O:36]>>[NH2:13][C:12]1[C:7]([C:5]([NH:4][N:19]=[CH:18][NH:23][P:25](=[O:36])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[O:6])=[N:8][C:9]([Cl:15])=[C:10]([NH2:14])[N:11]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 68530Ethyl phosphorochloridite

HCID 763491,5-Diazabicyclo(4.3.0)non-5-ene

HCID 178513083HCID 178513083, compound

Product 1

HCID 178476927HCID 178476927, 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 (300 ml.) is cooled to 10° C. and treated with diethyl chlorophosphite (2.9 ml., 0.02 mole). The reaction is stirred at 25° C. for 3 hours, filtered and treated with ice water (300 ml.) to give diethyl N-[(3,5-diamino-6-chloro-pyrazinamido)iminomethyl]phosphoramidate which melts at 230° C. after recrystallization from ethanol-water.

Workup

filtrationfiltered
additiontreated with ice water (300 ml.)

Sources & evidence

ORD record: ord-960ab3d9ab704cd8b07c05ab4008cd5d
Source dataset: uspto-grants-1979_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04163781

Linked notes

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