Sulfuric Acid → HCID 66823719, compound

HRID 1520750Notes

Reaction equation

[Br:1][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[N:5][C:4]=1[N+:12]([O-:14])=[O:13].S(=O)(=O)(O)[OH:16]>>[Br:1][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][C:10]([NH2:11])=[O:16])[CH:6]=[N:5][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 66823560HCID 66823560, compound

Product 1

HCID 66823719HCID 66823719, compound

Procedure

3-[5-(Bromomethyl)-4-nitro-1H-imidazol-1-yl]propanenitrile (115) (680 mg, 2.62 mmol) was treated with 90% sulphuric acid (5 mL) at 65-70° C. for 1 hour, before being poured onto ice. After a standard ethyl acetate/NaHCO3 workup, the crude product obtained was precipitated from THF by the addition of i-Pr2O to give 3-[5-(bromomethyl)-4-nitro-1H-imidazol-1-yl]propanamide (116) (420 mg, 58%) as an off-white solid, m.p. 139-141° C. 1H NMR (d6-DMSO) δ 7.90 (s, 1H), 7.44 (br, 1H), 7.00 (br, 1H), 5.06 (s, 2H), 4.32 (t, J=6.8 Hz, 2H), 2.70 (t, J=6.8 Hz, 2H). LR-MS (APCI +ve): m/e 277.5/279.5 (1:1, M+1).

Workup

additionbefore being poured onto ice

Sources & evidence

ORD record: ord-aeb2db07567344aa8aaa1f8bf5b8d18b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073916B2

Reaction notes

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