HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → N-[2-methoxy(methyl)amino-2-oxoethyl]-2-(trifluoromethyl)benzamide

HRID 56033
Notes
Print preview

Reaction equation

HRID 56033 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6].Cl.[CH3:19][NH:20]OC.Cl.[CH3:24]N(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:24][O:10][C:9](=[O:11])[CH:8]([NH:20][CH3:19])[NH:7][C:5](=[O:6])[C:4]1[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=1[C:2]([F:16])([F:17])[F:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167778182-((2-(Trifluoromethyl)phenyl)formamido)acetic acid

Product 1

HCID 118071607N-[2-methoxy(methyl)amino-2-oxoethyl]-2-(trifluoromethyl)benzamideYield 59.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 45.2 g of 2-[2-(trifluoromethyl)benzoylamino]acetic acid in 609 ml of dichloromethane, 21.4 g of N,O-dimethylhydroxylamine hydrochloride, 42.0 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 73.8 g of triethylamine and 2.2 g of 4-(dimethylamino)pyridine were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was washed with 500 ml of saturated anhydrous sodium hydrogen carbonate, 500 ml of 1N aqueous hydrochloric acid twice and 500 ml of water in this order, the resulting organic layer was dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was washed with 200 ml of hexane to obtain 31.4 g of the desired product as white crystals.

Workup

  1. customAfter completion of the reaction
  2. washthe reaction mixture was washed with 500 ml of saturated anhydrous sodium hydrogen carbonate, 500 ml of 1N aqueous hydrochloric acid twice
  3. dry with material500 ml of water in this order, the resulting organic layer was dried over saturated aqueous sodium chloride
  4. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  5. washThe resulting residue was washed with 200 ml of hexane

Sources & evidence

ORD record
ord-fc3ce71d56534995bb824e7f99629d9f
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434684B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes