Potassium Carbonate → HCID 67371851, compound

HRID 1676859Notes

Reaction equation

HRID 1676859 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10]O)=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:7][CH:6]1[I:18])[CH2:2][CH2:3][CH3:4].O=S(Cl)Cl.C(N1C(C[N:33](CC2C=CC3OCCOC=3C=2)[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH2:42][CH3:43])[CH:36]=2)=C(Cl)N=C1N1CCOCC1)CCC.C(ONCC1C=CC=CC=1)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CN(C=O)C>[CH2:1]([N:5]1[C:9]([CH2:10][NH:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH2:42][CH3:43])[CH:36]=2)=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:7][CH:6]1[I:18])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 18794272Benzyl(ethoxy)amineHCID 58786323HCID 58786323, compoundHCID 67370923HCID 67370923, compound

Product 1

HCID 67371851HCID 67371851, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(1-Butyl-2-iodo-4-phenyl-3H-imidazol-5-yl)-methanol (1.96 g), prepared by the method given in Example 2, step 2, is dissolved in 20 mL CH2Cl2. The solution is cooled to 0° C. and 3 equivalents of SOCl2 are added. The resulting solution is stirred at room temperature for 2 hours and then evaporated to dryness. The residue is dissolved in 5 mL of DMF and added to an ice cooled solution of 2 equivalents of 3 ethoxybenzylamine and 2 equivalents K2CO3 in 10 mL DMF. The mixture is stirred overnight at room temperature. The reaction is quenched with 20 mL water, extracted with EtOAc (3×30 mL), washed with water and brine, and dried over Na2SO4. Concentration and purification via silica gel chromatography provides (1-Butyl-2-iodo-4-phenyl-3H-imidazol-5-ylmethyl)-(3-ethoxy-benzyl)-amine.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in 5 mL of DMF
  3. stirringThe mixture is stirred overnight at room temperature
  4. customThe reaction is quenched with 20 mL water
  5. extractionextracted with EtOAc (3×30 mL)
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationConcentration and purification via silica gel chromatography

Sources & evidence

ORD record
ord-86478b18f6154a3aa3eee0af8667f325
Source dataset
uspto-grants-2011_08
Patent number
US08007767B2

Reaction notes

Loading…