Diethylamine → N,N-diethyl-4-iodobenzamide
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 5.
Workup
- additionwas added
- additionAfter the addition
- customthe resulting reaction mixture
- washwas then washed with saturated ammonium chloride
- extractionThe organic extract
- dry with materialwas dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customResidue was recrystallized from hot hexanes
Sources & evidence
- ORD record
- ord-28b78c804afd448ea22a9636a4b3cf3b
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07396834B2
Reaction notes
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