3-Iodobenzoic acid → HCID 16388679, compound

HRID 2357628Notes

Reaction equation

HRID 2357628 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C([N:13]([CH:17]([CH3:19])[CH3:18])C(C)C)C.C1(N)CC1>S(Cl)(Cl)=O.O1CCOCC1.C(OCC)(=O)C>[CH:17]1([NH:13][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 120603-Iodobenzoic acidHCID 69828CyclopropylamineHCID 81531Diisopropylethylamine

Product 1

HCID 16388679HCID 16388679, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

3-Iodobenzoic acid (4.79 g, 19.3 mmol) was suspended in thionyl chloride (19.3 mL) and stirred for 1 h at 70° C. before it was conc. and azeotropically dried with toluene. The reaction mixture was dissolved in dioxane (19.3 mL) before N-ethyl-N-isopropylpropan-2-amine (13.5 mL, 77.3 mmol) and cyclopropylamine (6.77 mL, 96.6 mmol) were added and stirred for 16 h at ambient temperature. The reaction mixture was diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2× with 50 mL of 3 N HCl (aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 288 (M+H)+.

Workup

  1. dry with materialazeotropically dried with toluene
  2. additionwere added
  3. stirringstirred for 16 h at ambient temperature
  4. additionadded to a separation funnel
  5. custompartitioned with sodium bicarbonate (saturated, aqueous)
  6. washwashed 2× with 50 mL of 3 N HCl (aqueous)
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83da322f2d5040fe97cad68a6ba273b8
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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