Sodium Carbonate → HCID 21285537, compound

HRID 2231655Notes

Reaction equation

HRID 2231655 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[F:8][C:9]([F:31])([F:30])[C:10]([N:12]([CH2:19][C:20]1[CH:25]=[C:24](F)[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>>[F:8][C:9]([F:30])([F:31])[C:10]([N:12]([CH2:19][C:20]1[CH:25]=[C:24]([N:3]2[CH:4]=[C:5]([CH3:7])[N:6]=[C:2]2[CH3:1])[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 21285511HCID 21285511, compoundHCID 178430880HCID 178430880, compound

Product 1

HCID 21285537HCID 21285537, compound

Procedure

A mixture of 2,4-dimethylimidazole (6.25 g), ethyl N-trifluoroacetyl-N-(5-fluoro-2-nitrobenzyl)glycinate (22.0 g) and sodium carbonate (6.62 g) was stirred and heated at 130° for 2 hours. Volatile material was removed from the cooled mixture in vacuo and the residue was partitioned between ethyl acetate (200 cm3) and water (100 cm3). The organic phase was washed with water (2×25 cm3), dried (MgSO4), and evaporated in vacuo to give an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate:methanol, 1:19. Combination and evaporation of the appropriate fractions gave an oil which crystallised on trituration with ether to afford the title compound, m.p. 172.5°-176° (3.1 g). Analysis %: Found: C,50.7; H,4.8; N,12.7; Calculated for C18H19F3N4O5 : C,50.5; H,4.5; N,13.1.

Workup

  1. temperatureheated at 130° for 2 hours
  2. customVolatile material was removed from the cooled mixture in vacuo
  3. customthe residue was partitioned between ethyl acetate (200 cm3) and water (100 cm3)
  4. washThe organic phase was washed with water (2×25 cm3)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto give an oil which
  8. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  9. washeluting with ethyl acetate
  10. customCombination and evaporation of the appropriate fractions
  11. customgave an oil which
  12. customcrystallised on trituration with ether

Sources & evidence

ORD record
ord-e18878f8af0a432e910575e99a78a2df
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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