N-Methylethylamine → HCID 14013813, compound

HRID 1763136Notes

Reaction equation

HRID 1763136 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]([Cl:15])([F:14])[F:13])[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].[CH2:25]([NH:27][CH3:28])[CH3:26]>CN(C=O)C>[Cl:15][C:12]([F:14])([F:13])[C:6]1[N:5]=[C:4]([C:16]([F:17])([F:19])[F:18])[C:3]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:2]([N:27]([CH2:25][CH3:26])[CH3:28])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 140137593-Ethyl 5-methyl 4-chloro-6-(chlorodifluoromethyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 14013813HCID 14013813, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared as described in Example 37: 5.0 g (0.013 mol) of product of Example 28, 1.54 g (0.026 mol) of N-ethylmethylamine in 30 ml of DMF were reacted at room temperature for 16 hours affording a residue which was kugelrohr distilled at 80 Pa, pot temperature 104° C., to give 4.7 g of oil. Purification by HPLC using 5% ethyl acetate/cyclohexane as eluting solvent afforded 4.0 g of oil which was purified by kugelrohr distillation at 67 Pa, pot temperature 107° C., to give 3.85 g (70.7%) of product as a yellow solid; mp 33°-35° C.

Workup

  1. customThis compound was prepared
  2. customaffording a residue which
  3. distillationwas kugelrohr distilled at 80 Pa, pot temperature 104° C.

Sources & evidence

ORD record
ord-70e5161fc7294d69815bf297a103da8c
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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