Diethylamine → N,N-Diethyl-3-iodobenzamide

HRID 741619Notes

Reaction equation

HRID 741619 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH2:17]([N:19]([CH2:20][CH3:21])[C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=1)[CH3:18]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 120603-Iodobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 4060936N,N-Diethyl-3-iodobenzamideYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Iodobenzoic acid (55.5 g, 0.224 mol) was dissolved in tetrahydrofuran (220 mL) and oxalyl chloride (22 mL, 0.252 mol). Catalytic dimethylformamide (4 drops) was added, the solution was stirred at room temperature for 1 hour, and the solvent was removed under vacuum. The residue was dissolved in 220 mL petroleum ether (35°-60° C. boiling range) and cooled to 0° C. in an ice bath. Diethylamine (55 mL, 0.532 mol) was then added dropwise over 15 minutes. The reaction mixture was stirred an additional 15 minutes in the ice bath, then diluted with ethyl acetate (100 mL) and washed with saturated sodium chloride solution (50 mL). The organic layer was separated, dried over magnesium sulfate, and concentrated in vacuo to approximately half of the original volume. The solution was then filtered through a small pad of silica gel, using ethyl acetate to wash the pad. All volatiles were removed in vacuo, and the product was dried under high vacuum to give 65.69 g (97%) of N,N-diethyl-3-iodobenzamide as an amber oil. NMR (300 MHz, CDCl3): δ1.11 (br s, 3H); 1.21 (br s, 3H); 3.23 (br s, 2H); 3.51 (br s, 2H); 7.13 (ddd, J1 =0.8 Hz, J2 =7.6 Hz, J3 =7.6 Hz, 1H); 7.32 (ddd, J1 =1.3 Hz, J2 =1.3 Hz, J3 =7.5 Hz, 1H); 7.71 (d, J=1.2 Hz, 1H); 7.72 (ddd, J1 =1.3 Hz, J2 =1.3 Hz, J3 =approx. 8.0 Hz (partially obstructed), 1H). Mass spectrum (CI--CH4) m/e: 304 (M+1, 100%). Calc. for C11H14NOI: C. 43.58; H, 4.65; N, 4.62; I, 41.86. Found: C, 43.68; H, 4.64; N, 4.64; I, 41.92.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in 220 mL petroleum ether (35°-60° C. boiling range)
  3. temperaturecooled to 0° C. in an ice bath
  4. washwashed with saturated sodium chloride solution (50 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo to approximately half of the original volume
  8. filtrationThe solution was then filtered through a small pad of silica gel
  9. washto wash the pad
  10. customAll volatiles were removed in vacuo
  11. customthe product was dried under high vacuum

Sources & evidence

ORD record
ord-10a26902aa5d419c9b6149e45ee94080
Source dataset
uspto-grants-1996_09
Patent number
US05552404

Reaction notes

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