Diethylamine → N,N-diethyl-4-iodobenzamide

HRID 1294729Notes

Reaction equation

HRID 1294729 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][CH2:12][N:13](CC)[CH2:14][CH3:15].N(CC)CC>C(Cl)Cl>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]([CH2:14][CH3:15])[CH2:12][CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 8471TriethylamineHCID 743734-Iodobenzoyl chloride

Product 1

HCID 875218N,N-diethyl-4-iodobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-iodo-benzoyl chloride (75 g) in 500 mL CH2Cl2 was added a mixture of Et3N (50 mL) and Et2NH (100 mL) at 0° C. After the addition, the resulting reaction mixture was warmed up to room temperature in 1 hr and was then washed with saturated ammonium chloride. The organic extract was dried (Na2SO4), filtered and concentrated. Residue was recrystallized from hot hexanes to give 80 g of INTERMEDIATE 1.

Workup

  1. additionwas added
  2. additionAfter the addition
  3. customthe resulting reaction mixture
  4. washwas then washed with saturated ammonium chloride
  5. extractionThe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customResidue was recrystallized from hot hexanes

Sources & evidence

ORD record
ord-7a11eae8c0c84705993e71fb1f54cd61
Source dataset
uspto-grants-2007_07
Patent number
US07241764B2

Reaction notes

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