Nitric Acid → HCID 67769393, compound

HRID 1898917Notes

Reaction equation

HRID 1898917 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[CH2:5]([N:7]([C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[F:35])[C:8]([C:10]1[C:11]([NH2:24])=[N:12][C:13]([N:16]2[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]2=[O:23])=[N:14][CH:15]=1)=[O:9])[CH3:6]>C(OCC)(=O)C>[N+:1]([O-:4])([OH:3])=[O:2].[CH2:5]([N:7]([C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[F:35])[C:8]([C:10]1[C:11]([NH2:24])=[N:12][C:13]([N:16]2[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]2=[O:23])=[N:14][CH:15]=1)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 54093636HCID 54093636, compound2×

Product 1

HCID 67769393HCID 67769393, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2.05 ml of a molar solution of HNO3 in ethyl acetate were added to a suspension of 881 mg (2 mmol) of 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-ethyl-N-(2-fluoro-5-trifluoromethylphenyl)amide (compound I from Example 17) in 13.3 ml of ethyl acetate at room temperature. This briefly resulted in a solution, from which a crystalline substance separated out. The latter was, after stirring (in an ice bath) for 1 hour, filtered off with suction, washed with ethyl acetate and ether and dried at 80° in vacuo (6-8 mbar) for 15 hours. 1.02 g of 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-ethyl-N-(2-fluoro-5-trifluoromethylphenyl)amide nitrate were obtained, melting point 235°-236°. This nitrate is soluble in a concentration of 1.7% by weight in water, i.e. 1 part dissolves in 57.5 parts of water.

Workup

  1. customThis briefly resulted in a solution, from which a crystalline substance
  2. customseparated out
  3. filtrationfiltered off with suction
  4. washwashed with ethyl acetate and ether
  5. customdried at 80° in vacuo (6-8 mbar) for 15 hours

Sources & evidence

ORD record
ord-ec22f9d615db40de9784f4e8a821413a
Source dataset
uspto-grants-1996_11
Patent number
US05571816

Reaction notes

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