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

HRID 21257Notes

Reaction equation

HRID 21257 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][O:13][CH3:14])[C:5]([OH:7])=O.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:37]([NH2:46])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([CH3:39])[CH3:38]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][O:13][CH3:14])[C:5]([NH:46][C:37]([CH3:39])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:38])=[O:7]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 579866883-Chloro-4-methoxymethoxybenzoic acid

Product 1

HCID 684890703-chloro-4-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamideYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 137, 3-chloro-4-methoxymethoxybenzoic acid (2.39 g, 11.0 mmol) was dissolved in DMF (47 mL), and the solution was treated with EDCI (4.23 g, 22.1 mmol), HOBT monohydrate (1.69 g, 11.0 mmol) and cumylamine (3.20 mL, 22.0 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-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide (2.83 g, yield 77%).

Workup

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

Sources & evidence

ORD record
ord-01bcbb278b5d45e0879f5b73eff2fb3e
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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