Water → HCID 13882887, compound

HRID 542123Notes

Reaction equation

HRID 542123 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[F:6][C:7]([F:25])([F:24])[C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12](Cl)[CH:11]=[C:10]([C:20]([F:23])([F:22])[F:21])[N:9]=1.O>CN(C=O)C>[CH2:1]([N:3]([CH2:4][CH3:5])[C:12]1[CH:11]=[C:10]([C:20]([F:23])([F:22])[F:21])[N:9]=[C:8]([C:7]([F:25])([F:24])[F:6])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 13882887HCID 13882887, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethylamine (2.1 ml, 0.020 mol) was slowly added to a solution of 3.0 g (0.009 mol) of product of Example 19 in 15 ml of DMF and stirred overnight. Reaction mixture was poured into water, extracted with ether, washed with water, dried (MgSO4) and concentrated. The residue was kugelrohr distilled twice at 28 Pa, pot temperature 76° C., to afford 2.06 g (63.2%) of product as a yellow oil, nD25 1.4593.

Workup

  1. customReaction mixture
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. distillationThe residue was kugelrohr distilled twice at 28 Pa, pot temperature 76° C.

Sources & evidence

ORD record
ord-132b2d2d69934644819bca610590a2d4
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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