Hydrochloric Acid → HCID 15376209, compound

HRID 374580Notes

Reaction equation

HRID 374580 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][NH2:11])=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12](=S)=[S:13].OO.Cl>C(#N)C.O>[Cl:1][C:2]1[C:3]2[N:4]([C:12](=[S:13])[NH:11][N:10]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 6348Carbon DisulfideHCID 15376210HCID 15376210, compound

Product 1

HCID 15376209HCID 15376209, compoundYield 142%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-4-hydrazino-2-methoxypyrimidine (17.45 g, 0.10 mol) and 25 g (0.033 mol) of carbon disulfide were combined in 120 mL of acetonitrile and 30 mL of water at ambient temperature with stirring and 11.4 g (0.10 mol) of 30 percent hydrogen peroxide was added to the resulting mixture with stirring over a 2-hour period. The temperature rose from 20° C. to 48° C. Analysis of the mixture by high pressure liquid chromatography (HPLC) indicated that the reaction was complete. A 79.8 g (47.2 percent of the total) portion of the reaction mixture was diluted with 50 mL of water and the mixture was acidified with hydrochloric acid. The solids present were then recovered by vacuum filtration and dried to obtain 10.15 g of a mixture of the title compound and sulfur. The sulfur was then removed by extracting the solids with 45 g of carbon disulfide to obtain 8.08 g (80 percent of theory) of the title compound as a tan powder. This material was 92 percent pure by HPLC analysis; it decomposed on heating.

Workup

  1. customrose from 20° C. to 48° C
  2. filtrationThe solids present were then recovered by vacuum filtration
  3. customdried

Sources & evidence

ORD record
ord-3635b5164cb44084a7f52e1df9cf643e
Source dataset
uspto-grants-1996_01
Patent number
US05480991

Reaction notes

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