Dimethylformamide → Benzamide

HRID 1645727Notes

Reaction equation

HRID 1645727 reaction equation
Cl.C(N=C=NCCCN(C)C)C.O[C:14]1[C:22]2N=NN[C:18]=2[CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C.C[N:33]([CH:35]=[O:36])C>>[C:35]([NH2:33])(=[O:36])[C:14]1[CH:22]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 2331Benzamide

Procedure

Ester compound 3 is converted to the free carboxylic acid, and is then reacted with substituted aniline compound 4 to yield an arylamide of formula 5. For example, LiOH is added to a stirred solution of 3 in a mixture of solvents. The volatiles are removed under vacuum, and the residue is diluted with water and acidified to about pH 3. The resulting solids are filtered, washed with water and dried under vacuum to furnish a carboxylic acid intermediate. The intermediate is dissolved in a solvent such as DMF and the mixture is stirred to prepare a solution. To the stirred solution is added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) followed by hydroxybenzotriazole (HOBt). After stirring, diisopropyl ethyl amine is added and stirred. Then substituted aniline 4 (representative of substituted aryl or heteroaryl) is added, and the reaction mixture is stirred. The solvent is removed under vacuum. The residue is diluted with water and stirred. The resulting solids are filtered and purified through column chromatography to provide benzamide compound 5.

Workup

  1. customto prepare a solution
  2. stirringAfter stirring
  3. stirringstirred
  4. stirringthe reaction mixture is stirred
  5. customThe solvent is removed under vacuum
  6. additionThe residue is diluted with water
  7. stirringstirred
  8. filtrationThe resulting solids are filtered
  9. custompurified through column chromatography

Sources & evidence

ORD record
ord-f39ec0a043614b59937131cd2664b661
Source dataset
uspto-grants-2012_02
Patent number
US08124764B2

Reaction notes

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