Triethylamine → N-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-2-furancarboxamide

HRID 986999Notes

Reaction equation

HRID 986999 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][NH2:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(CC)CC)C.[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](Cl)=[O:27]>O1CCCC1>[Cl:1][C:2]1[C:3]([CH2:12][NH:13][C:26]([C:22]2[O:21][CH:25]=[CH:24][CH:23]=2)=[O:27])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 11085087(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)methanamine

Product 1

HCID 22988184N-[[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-2-furancarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (3-chloro-5-trifluoromethyl-2-pyridyl)methylamine (1 mmol) in tetrahydrofuran (5 ml) was added triethylamine (1 mmol) at room temperature and the mixture was stirred at room temperature for 1.5 hour. The mixture was added to a solution of 2-furoyl chloride (1 mmol) in tetrahydrofuran (5 ml) at room temperature and left to stir at room temperature overnight. The mixture was evaporated to dryness and the residue washed with water. The solid was filtered, washed with diethyl ether/light petroleum (b.p. 60-80° C.) and dried to give the title product, 1H N.M.R. (CDCl3) δ (ppm) 4.9 (2H, d), 6.55 (1H, m), 7.2 (1H, m), 7.5 (1H, s), 7.8 (1H, br.s), 8.0 (1H, s) and 8,8 (1H, s).

Workup

  1. waitleft
  2. stirringto stir at room temperature overnight
  3. customThe mixture was evaporated to dryness
  4. washthe residue washed with water
  5. filtrationThe solid was filtered
  6. washwashed with diethyl ether/light petroleum (b.p. 60-80° C.)
  7. customdried

Sources & evidence

ORD record
ord-10d612dd35b54d26955da581da18be2c
Source dataset
uspto-grants-2003_10
Patent number
US06630495B1

Reaction notes

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