Acetic Acid → HCID 86666627, compound

HRID 587842Notes

Reaction equation

HRID 587842 reaction equation
[NH2:1][CH:2]([C:4]1[CH:31]=[CH:30][C:7]([C:8]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([C:18]([F:27])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])=[CH:13][C:12]=2[CH2:28][CH3:29])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[C:32](O)(=[O:34])[CH3:33].Cl.C(N=C=NCCCN(C)C)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:32]([NH:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([C:18]([F:27])([C:19]([F:20])([F:21])[F:22])[C:23]([F:24])([F:25])[F:26])=[CH:13][C:12]=2[CH2:28][CH3:29])=[O:9])=[CH:30][CH:31]=1)[CH3:3])(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86666625HCID 86666625, compound

Product 1

HCID 86666627HCID 86666627, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(1-Aminoethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]benz amide (0.4 g) was dissolved in methylene chloride (15 ml). To the solution, acetic acid (0.06 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.26 g) and an catalytic amount of dimethylaminopyridine were added and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure and the residue was added with water followed by extraction twice with ethyl acetate. The organic phases were combined, washed with water and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain 4-(1-acetamidoethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)-6-methylphenyl]benzamide (0.35 g, yield 95%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was added with water
  3. extractionfollowed by extraction twice with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-69d98e4b17a747ed9c09d4cd7016898d
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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