Dimethyl Sulfoxide → HCID 178478697, compound

HRID 1422449Notes

Reaction equation

HRID 1422449 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]=[C:9]([NH2:12])[NH:10][CH:11]=1.CS(C)=[O:15]>C(OCC)C>[ClH:1].[ClH:1].[NH2:12][C:9]1[NH:8][C:7](=[CH:6][CH2:5][CH2:4][NH2:3])[C:11](=[O:15])[N:10]=1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 178478696HCID 178478696, compound

Product 1

HCID 178478697HCID 178478697, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(3-amino-propyl)-1H-imidazol-2-ylamine 16 (0.200 g, 0.930 mmol) was dissolved in anhydrous dimethyl sulfoxide (6 mL) Bromine (0.047 mL, 0.930 mmol) was added drop-wise and the solution was stirred at room temperature for 1 h. Diethyl ether (7 mL) was added and the organics were then decanted. The residue was purified by column chromatography (MeOH sat. with NH3) to yield the desired product as its free base. Addition of concentrated hydrochloric acid to a methanol solution (8 mL) of the free base followed by evaporation under reduced pressure afforded the target compound ((Z)-isomer exclusively) (0.141 g, 67%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 12.10 (br s, 1H), 9.20 (br s, 2H), 8.18 (br s, 2H), 5.92 (t, 1H, J=7.8 Hz), 2.96 (m, 2H), 2.66 (m, 2H); 13C NMR (100 MHz, DMSO-d6) δ 164.13, 156.63, 130.88, 113.70, 37.57, 24.94; HRMS (FAB) calcd for C6H10N4O (MH+) 155.0933, found 155.0943.

Workup

  1. additionwas added drop-wise
  2. customthe organics were then decanted
  3. customThe residue was purified by column chromatography (MeOH sat. with NH3)

Sources & evidence

ORD record
ord-a43f8067c7504321bcdbb6628f38d3dc
Source dataset
uspto-grants-2015_01
Patent number
US08927029B2

Reaction notes

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