Cyclohexanol → HCID 66631016, compound

HRID 2382342Notes

Reaction equation

HRID 2382342 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH3:6][O:7][C:8](=[O:18])[CH2:9][N:10]1[CH:14]=[C:13]([CH2:15][CH2:16][NH2:17])[N:12]=[CH:11]1.[CH:19]1(O)[CH2:24][CH2:23]C[CH2:21][CH2:20]1>S(=O)(=O)(O)O>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH:6]1([O:7][C:8](=[O:18])[CH2:9][N:10]2[CH:14]=[C:13]([CH2:15][CH2:16][NH2:17])[N:12]=[CH:11]2)[CH2:23][CH2:24][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 7966CyclohexanolHCID 66630884HCID 66630884, compound

Product 1

HCID 66631016HCID 66631016, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
110 °C

Procedure

[4-(2-Amino-ethyl)-imidazol-1-yl]-acetic acid methyl ester sulphate (1 g, 3.6 mmol) is suspended in cyclohexanol (50 ml) and treated with concentrated sulphuric acid (5 drops). The reaction mixture is heated to 110° C. for 4 hours and concentrated in vacuo. The residue is dissolved in saturated sodium bicarbonate solution and the mixture is concentrated in vacuo. The resulting solid is triturated with methanol, filtered and the filtrate is reduced in vacuo. The crude solid is dissolved in water, washed with DCM and the aqueous portion is concentrated in vacuo to yield the title product.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in saturated sodium bicarbonate solution
  3. concentrationthe mixture is concentrated in vacuo
  4. customThe resulting solid is triturated with methanol
  5. filtrationfiltered
  6. dissolutionThe crude solid is dissolved in water
  7. washwashed with DCM
  8. concentrationthe aqueous portion is concentrated in vacuo

Sources & evidence

ORD record
ord-77d3f12437f348ec85df447184c90c39
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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