Chloro-N,N-dimethylformiminium chloride → Hydrochloric Acid

HRID 2288237Notes

Reaction equation

HRID 2288237 reaction equation
S(O)(O)(=O)=O.NC1N=C(O)C(N)=C(O)N=1.NC1N=C(O)C(N)=C(O)N=1.C[N+](C)=C[Cl:29].[Cl-].[Cl:32][C:33]1[C:38]([N:39]=[CH:40][N:41]([CH3:43])[CH3:42])=[C:37]([Cl:44])[N:36]=[C:35]([N:45]=CN(C)C)[N:34]=1>C(O)C>[ClH:29].[NH2:45][C:35]1[N:34]=[C:33]([Cl:32])[C:38]([N:39]=[CH:40][N:41]([CH3:42])[CH3:43])=[C:37]([Cl:44])[N:36]=1

Participants

6

Reactant 3

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 540126124,6-Dichloro-2,5-bis-{[(dimethylamino)methylene]amino}pyrimidineHCID 178508995HCID 178508995, compound

Product 2

HCID 313Hydrochloric AcidHCID 11107249N'-(2-Amino-4,6-dichloro-5-pyrimidinyl)-N,N-dimethylmethanimidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In another experiment, 2,5-diamino-4,6-dihydroxypyrimidine hemisulfate (Sigma, 48.0 g, 0.250 mole) was reacted as in Example 1 with less Vilsmeier reagent (7.2 molar equivalents) and the resulting 4,6-dichloro-2,5-bis-{[(dimethylamino)methylene]amino}pyrimidine (92%), without recrytallizaton, was hydrolyzed in 95% ethanol (1 L) and 6 N aqueous hydrochloric acid (110 mL) to provide the title compound of the same purity (elemental analysis and 1H-NMR) as the characterized sample described above (44.2 g. 76% overall from 2,5-diamino-4,6-dihydroxypyrimidine hemisulfate).

Sources & evidence

ORD record
ord-98a44c235d224d8488482c29b52b1352
Source dataset
uspto-grants-2000_07
Patent number
US06087501

Reaction notes

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