1-Aminocyclopropane-1-carboxylic acid → 1-({[4-Cyano-3-(trifluoromethyl)phenyl]carbamoyl}amino)cyclopropanecarboxylic acid

HRID 468579Notes

Reaction equation

HRID 468579 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)=[C:2]=[O:3].[NH2:16][C:17]1([C:20]([OH:22])=[O:21])[CH2:19][CH2:18]1.[OH-].[Na+]>CC(C)=O.C(OCC)C>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([NH:1][C:2]([NH:16][C:17]2([C:20]([OH:22])=[O:21])[CH2:19][CH2:18]2)=[O:3])=[CH:5][C:6]=1[C:12]([F:13])([F:14])[F:15])#[N:9]

Participants

6

Reactant 3

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 14798Sodium Hydroxide2×HCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrile

Product 1

HCID 667518161-({[4-Cyano-3-(trifluoromethyl)phenyl]carbamoyl}amino)cyclopropanecarboxylic acidYield 50%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-isocyanato-2-(trifluoromethyl)benzonitrile (4.56 g, 21.5 mmol) in acetone (12 ml) is added dropwise to 1-aminocyclopropane carboxylic acid (2.02 g, 20 mmol) dissolved in an aqueous solution of sodium hydroxide (12 ml, 0.8 g, 20 mmol). The reaction medium is stirred for 1 hour at ambient temperature then poured into an aqueous solution of sodium hydroxide (1N, 40 ml). The solution obtained is washed with ethyl acetate (30 ml) then acidified by the addition of an aqueous solution of sulphuric acid (2M, 30 ml) and extracted with ethyl acetate (2×50 ml). The organic phase thus obtained is washed with water then with a saturated aqueous solution of sodium chloride, dried over Na2SO4 and filtered. The solvent is evaporated off under reduced pressure. The residue obtained is taken up in ethyl ether in order to produce a white solid, after filtration, with a yield of 50% (3.16 g).

Workup

  1. customThe solution obtained
  2. washis washed with ethyl acetate (30 ml)
  3. additionthen acidified by the addition of an aqueous solution of sulphuric acid (2M, 30 ml)
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. customThe organic phase thus obtained
  6. washis washed with water
  7. dry with materialwith a saturated aqueous solution of sodium chloride, dried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent is evaporated off under reduced pressure
  10. customThe residue obtained
  11. customto produce a white solid
  12. filtrationafter filtration

Sources & evidence

ORD record
ord-395366e3bd8740c1b1a977b472dbab2e
Source dataset
uspto-grants-2014_01
Patent number
US08624037B2

Reaction notes

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