Water → HCID 178510563, compound

HRID 2211161Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[C:9]([C:12]([NH2:14])=O)[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[C:1]1([C:7]2[N:8]=[C:9]([C:12]#[N:14])[NH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A suspension of 4.55 g of 4-phenyl-1H-imidazole-2-carboxamide in pyridine (30 ml) was stirred and cooled to -20° C. and treated dropwise with phosphorous oxychloride (2.3 ml) keeping the internal temperature below 0° C. After 40 min the reaction mixture was cooled to -25° C. and water (5 ml) was slowly added. The resultant suspension was poured into stirred water, carefully basified with potassium carbonate, and then filtered. The filtered solid was dissolved in dichloromethane and passed through a short column of fine silica. The column was eluted with dichloromethane-ethyl acetate (9:1), the appropriate fractions were collected and evaporated to give 4-phenyl-1H-imidazole-2-carbonitrile (2.02 g), which was treated in the manner as described in Example 3b and converted with methanesulphone acid into N-hydroxy-4-phenyl-1H-imidazole-2carboximidamide methanesulphonate (1:2), m.p. 151°-153° C.

Workup

customthe internal temperature below 0° C
temperatureAfter 40 min the reaction mixture was cooled to -25° C.
filtrationfiltered
dissolutionThe filtered solid was dissolved in dichloromethane
washThe column was eluted with dichloromethane-ethyl acetate (9:1)
customthe appropriate fractions were collected
customevaporated

Sources & evidence

ORD record: ord-0e47f1d694084b88a19b7188cd3490aa
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05462959

Reaction notes

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