1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-chloro-4-methyl-N-(1-methyl-1-phenylethyl)benzamide

HRID 21247Notes

Reaction equation

HRID 21247 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:34]([NH2:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:36])[CH3:35]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:43][C:34]([CH3:36])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:35])=[O:7]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 788403-Chloro-4-methylbenzoic AcidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 684932213-chloro-4-methyl-N-(1-methyl-1-phenylethyl)benzamideYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 137, 3-chloro-4-methylbenzoic acid (1.00 g, 5.86 mmol) was dissolved in DMF (20 mL), and the solution was treated with EDCI (2.25 g, 11.7 mmol), HOBT monohydrate (792 mg, 5.86 mmol) and cumylamine (1.69 mL, 11.7 mmol). The reaction mixture was added with water. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure. The obtained solid was purified by slurry using diisopropylether to obtain 3-chloro-4-methyl-N-(1-methyl-1-phenylethyl)benzamide (1.64 g, yield 97%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customby drying under reduced pressure
  4. customThe obtained solid was purified by slurry

Sources & evidence

ORD record
ord-fefce322f23643309993e528cf8bb506
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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