1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66879593, compound

HRID 2190807Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[CH3:13][C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].CCN=C=NCCCN(C)C>N1C=CC=CC=1>[OH:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[NH:1][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][N:21]=[CH:22][C:14]=1[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.62 g of 2-amino-4-(trifluoromethyl)phenol, 0.48 g of 3-methyl isonicotinic acid, 0.86 g of WSC and 5 ml of pyridine was stirred while heating at 60° C. for three hours. The reaction mixture was cooled to room temperature, and then the reaction mixture was concentrated. Water was poured into the residue, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, sequentially. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was washed with a mixture solvent of tert-butyl methyl ether and hexane to give 0.38 g of N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3-methylisonicotinamide.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationthe reaction mixture was concentrated
additionWater was poured into the residue
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
washThe residue was washed with a mixture solvent of tert-butyl methyl ether and hexane

Sources & evidence

ORD record: ord-6e5615d25a52499f9dcdb5f05aeaa70c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324387B2

Reaction notes

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