Dimethyl Sulfoxide → HCID 18507323, compound

HRID 1356081Notes

Reaction equation

HRID 1356081 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[CH:8][CH:7]=1)=O)C.[CH2:11]([Li])[CH2:12][CH2:13]C.[H-].[Na+].CI.[N+:20]([O-])(O)=O.[NH2:24][C:25]([NH2:27])=[NH:26].C[S:29]([CH3:31])=O>C1COCC1.CN(C=O)C.C(N(CC)CC)C.C(=S)=S.C(#N)C>[NH2:26][C:25]1[N:27]=[C:4]([C:6]2[O:10][N:9]=[CH:8][CH:7]=2)[C:12]([C:13]#[N:20])=[C:11]([S:29][CH3:31])[N:24]=1

Participants

12

Reactant 6

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 10481Guanidine NitrateHCID 24758Sodium hydrideHCID 10701915Ethyl 1,2-oxazole-5-carboxylateHCID 178418339Butyllithium

Product 1

HCID 18507323HCID 18507323, compound

Reagents, catalysts & solvents 5

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6348Carbon DisulfideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

From isoxazole-5-carboxylic acid ethyl ester with acetonitrile and butyllithium in THF. Then treatment with sodium hydride, carbon disulphide and methyl iodide in DMSO. Then treatment with guanidine nitrate and triethylamine in DMF. EI-MS m/e (%): 233 (M+, 45), 206 ([M—HCN]+, 100), 151 (33).

Sources & evidence

ORD record
ord-bb8269a6dd3d47bcbaf68dcba639993c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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