Urea → HCID 57753350, compound

HRID 1930824Notes

Reaction equation

HRID 1930824 reaction equation
F[C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[C:5](=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])C(O)=O.N[C:19]([NH2:21])=[O:20].C[N:23]1CCCC1=O>C(OCC)(=O)C>[NH2:23][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:19](=[O:20])[NH:21][C:15]2=[O:17]

Participants

5

Reactant 3

HCID 1176UreaHCID 13387N-methyl-2-pyrrolidoneHCID 577536504-Fluoro-5-(trifluoromethyl)-1,2-benzenedicarboxylic acid

Product 1

HCID 57753350HCID 57753350, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2.14 mmol 4-fluoro-5-trifluoromethyl-phthalic acid in 7 ml N-methylpyrolidone was added 4.28 mmol urea and the mixture was at 140° C. for 2 h, and then at 160° C. for 4 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate and washed sequentially with water and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether/penane (1/1) to yield the title compound as a yellow solid. MS (m/e): 229.1 ([M−H]−, 100%)

Workup

  1. waitat 160° C. for 4 h
  2. washwashed sequentially with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in ether/penane (1/1)

Sources & evidence

ORD record
ord-378d100a3b724c5fbf570f6cf8405905
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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