Ethyl Acetate → HCID 68158303, compound

HRID 511818Notes

Reaction equation

HRID 511818 reaction equation
[Br:1][CH2:2][C:3]1[N:7]([CH3:8])[C:6]([C:9]#[N:10])=[N:5][C:4]=1[N+:11]([O-:13])=[O:12].C(OCC)(=[O:16])C>OS(O)(=O)=O.O>[Br:1][CH2:2][C:3]1[N:7]([CH3:8])[C:6]([C:9]([NH2:10])=[O:16])=[N:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68158987HCID 68158987, compound

Product 1

HCID 68158303HCID 68158303, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole-2-carbonitrile (264) (70 mg, 0.29 mmol) in 90% H2SO4 (1 mL) was heated at 65-70° C. for 1 hour, before being diluted with water and given a standard ethyl acetate workup to give 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole-2-carboxamide (266) (67 mg, 84%), as white solid, m.p. 220-222° C. 1H NMR [(CD3)2SO] δ 8.18 (s, 1H), 7.87 (s, 1H), 5.05 (s, 2H), 4.02 (s, 3H). HR-MS (APC+, 79/81Br) found: m/z 262.9770/264.9752 (M+1), calcd. for C6H879/81BrN4O3+: 262.9774/264.9754.

Sources & evidence

ORD record
ord-e33b66e854ae46529c8f7deff2ed7219
Source dataset
uspto-grants-2015_08
Patent number
US09101632B2

Reaction notes

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