Dimethylformamide → HCID 67372367, compound

HRID 1676858Notes

Reaction equation

HRID 1676858 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(N)C1C=[CH:31][C:30]2[O:29][CH2:28][O:27][C:26]=2C=1.C[N:35](C=O)C>C(Cl)Cl>[O:29]1[C:30]([CH2:31][NH:35][CH2:10][C:9]2[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]([I:18])[NH:7][C:8]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:26][O:27][CH2:28]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 67370923HCID 67370923, compound

Product 1

HCID 67372367HCID 67372367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-Butyl-2-iodo-4-phenyl-3H-imidazol-5-yl)-methanol (1.96 g) is dissolved in 20 mL of CH2Cl2. 5 equivalents of SOCl2 are added at 0° C. The solution is stirred at room temperature for 2 hours and then evaporated to dryness. The residue is dissolved in 20 mL of toluene and again evaporated to dryness in order to remove the remaining SOCl2. The crude product is dissolved in 5 mL DMF and added to an ice-cold solution of piperonyl amine (2 equivalents) in 10 mL DMF containing 2.0 equivalents K2CO3. The reaction mixture is stirred overnight at room temperature. The reaction is quenched with 20 mL water, extracted with ethyl acetate (3×30 mL), washed with water and brine, and dried over Na2SO4. Concentration and purification by silica gel chromatography gives [1,3]dioxol-5-ylmethyl-(1-butyl-2-iodo-4-phenyl-3H-imidazol-5-ylmethyl)-amine.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in 20 mL of toluene
  3. customagain evaporated to dryness in order
  4. customto remove the remaining SOCl2
  5. dissolutionThe crude product is dissolved in 5 mL DMF
  6. stirringThe reaction mixture is stirred overnight at room temperature
  7. customThe reaction is quenched with 20 mL water
  8. extractionextracted with ethyl acetate (3×30 mL)
  9. washwashed with water and brine
  10. dry with materialdried over Na2SO4
  11. concentrationConcentration and purification by silica gel chromatography

Sources & evidence

ORD record
ord-f051fefa140e4f1cb0a0c04bb904d5d0
Source dataset
uspto-grants-2011_08
Patent number
US08007767B2

Reaction notes

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