Ammonia → Methacrylic acid 1-aminocarbonyl-1,1-difluoro-2-butyl ester

HRID 2047585Notes

Reaction equation

HRID 2047585 reaction equation
[NH3:1].Cl[C:3]([C:5]([F:16])([F:15])[CH:6]([O:9][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])[CH2:7][CH3:8])=[O:4]>>[NH2:1][C:3]([C:5]([F:16])([F:15])[CH:6]([O:9][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])[CH2:7][CH3:8])=[O:4]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 58352381Methacrylic acid 1-chlorocarbonyl-1,1-difluoro-2-butyl ester

Product 1

HCID 58571378Methacrylic acid 1-aminocarbonyl-1,1-difluoro-2-butyl esterYield 90.9%

Procedure

In a 25-mL glass flask with a dropping funnel, 5.0 g (82.2 mmol/4.0 eq) of 28% aqueous ammonia solution was added and stirred. Subsequently, 5.0 g (purity: 98%, 20.4 mmol) of methacrylic acid 1-chlorocarbonyl-1,1-difluoro-2-butyl ester was dropped into the glass flask. The resulting solution was stirred for 10 minutes at room temperature. The completion of the reaction was confirmed by 19F NMR. After that, the solution was separated into an organic layer and an aqueous layer with the addition of 5 mL of water and 5 mL of diisopropyl ether. The thus-obtained aqueous layer was concentrated under a reduced pressure. With this, 4.1 g of methacrylic acid 1-aminocarbonyl-1,1-difluoro-2-butyl ester was obtained as a white crystalline substance (yield: 86%, purity: 96%).

Workup

  1. stirringThe resulting solution was stirred for 10 minutes at room temperature
  2. customAfter that, the solution was separated into an organic layer
  3. additionan aqueous layer with the addition of 5 mL of water and 5 mL of diisopropyl ether
  4. concentrationThe thus-obtained aqueous layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-c9f254c5ed7b4aafbabde830035eb852
Source dataset
uspto-grants-2013_11
Patent number
US08592540B2

Reaction notes

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