1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68492049, compound

HRID 21268Notes

Reaction equation

HRID 21268 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=O.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:38]([NH2:47])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([CH3:40])[CH3:39]>CN(C=O)C.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([NH:47][C:38]([CH3:40])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH3:39])=[O:10]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 653645693-Methoxymethoxy-4-methoxybenzoic acid

Product 1

HCID 68492049HCID 68492049, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 11 of Example 137, 3-methoxymethoxy-4-methoxybenzoic acid (6.41 g, 30.2 mmol) was dissolved in DMF (100 mL), and the solution was treated with EDCI (5.75 g, 30.0 mmol), HOBT monohydrate (4.05 g, 30.0 mmol) and cumylamine (8.63 mL, 60.0 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-methoxymethoxy-4-methoxy-N-(1-methyl-1-phenylethyl)benzamide (7.89 g, yield 80%).

Workup

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

Sources & evidence

ORD record
ord-d596d22586644dc893e7c00b6daba2d3
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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