2-Methylaziridine → HCID 14013828, compound

HRID 255435

Reaction equation

HRID 255435 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 14013828HCID 14013828, compoundYield 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-d3a14a3b8a0c4165a31ac5e41c94fc5f
Source dataset
uspto-grants-1987_10
Patent number
US04698093

Linked notes

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