2-Methylaziridine → 3-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(2-methylaziridinyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 1763147Notes

Reaction equation

HRID 1763147 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].C([N:27]([CH2:30][CH3:31])[CH2:28]C)C.C([O-])([O-])=O.[K+].[K+].CC1NC1>O.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]2[CH2:28][CH:30]2[CH3:31])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 63772-MethylaziridineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 140137593-Ethyl 5-methyl 4-chloro-6-(chlorodifluoromethyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 140138283-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(2-methylaziridinyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylateYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 50 ml of DMF was added 5.0 g (0.0126 mol) of product of Example 28, followed by 1.27 g (0.0126 mol) of triethylamine and 1.74 g (0.0126 mol) of K2CO3. To this mixture was added 0.922 g (0.0161 mol) of propyleneimine. This reaction mixture was stirred under N2 for 48 hours at room temperature. The reaction mixture was then poured into H2O and extracted with diethyl ether. The ether phase was then washed with H2O, and dried over MgSO4. The dry ether phase was then concentrated in vacuo to a crude yield of 4.8 g of a brown oil. This oil was kugelrohr distilled at 105° C./53 Pa, to yield 4.0 g of a yellow oil (76%), nD25 1.4763.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether phase was then washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationThe dry ether phase was then concentrated in vacuo to a crude yield of 4.8 g of a brown oil
  5. distillationThis oil was kugelrohr distilled at 105° C./53 Pa

Sources & evidence

ORD record
ord-929a94ef3e6a4e6db81bb6ad9778820b
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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