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

HRID 21243Notes

Reaction equation

HRID 21243 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:35]([NH2:44])([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([CH3:37])[CH3:36]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:44][C:35]([CH3:37])([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:36])=[O:7]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 1699823-Chloro-p-anisic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 684891313-chloro-4-methoxy-N-(1-methyl-1-phenylethyl)benzamideYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 137, 3-chloro-4-methoxybenzoic acid (1.00 g, 5.36 mmol) was dissolved in DMF (20 mL), and the solution was treated with EDCI (2.06 g, 10.7 mmol), HOBT monohydrate (724 mg, 5.36 mmol) and cumylamine (1.54 mL, 10.7 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 to obtain 3-chloro-4-methoxy-N-(1-methyl-1-phenylethyl)benzamide (1.59 g, yield 97%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customby drying under reduced pressure

Sources & evidence

ORD record
ord-40b735be436244ed95f8f35469bd7365
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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