m-Chloroperbenzoic acid → HCID 86650547, compound

HRID 2066651Notes

Reaction equation

HRID 2066651 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C:12]([CH3:14])=[CH2:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>>[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C:12]2([CH3:14])[CH2:13][O:23]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66956087HCID 66956087, compound

Product 1

HCID 86650547HCID 86650547, compoundYield 88%

Procedure

Epoxidation of alkene 139 with 3-chloroperbenzoic acid as in Example 2G for 4 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 0-5% EtOAc/CH2Cl2, gave 2-chloro-1-[2-(2-methyl-2-oxiranyl)ethyl]-4-nitro-1H-imidazole (140) (88%) as a cream solid: mp (CH2Cl2/pentane) 82-85° C.; 1H NMR (CDCl3) δ 7.78 (s, 1H), 4.12 (t, J=7.6 Hz, 1H), 2.66 (d, J=4.4 Hz, 1H), 2.62 (d, J=4.4 Hz, 1H), 2.19 (dt, J=14.3, 7.7 Hz, 1H), 2.04 (dt, J=14.3, 7.4 Hz, 1H), 1.39 (s, 3H); HRFABMS calcd for C8H11ClN3O3 m/z [M+H]+ 234.0459, 232.0489. found 234.0466, 232.0488.

Workup

  1. washeluting with CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-3ec9d4c1cbbf4ec9a950a46cb2d7dea7
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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