3-(Trifluoromethyl)phenyl isocyanate → HCID 11438779, compound

HRID 2262761Notes

Reaction equation

HRID 2262761 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15]([N:19]=[C:20]=[O:21])[CH:16]=[CH:17][CH:18]=1>CS(C)=O>[F:11][C:12]([F:22])([F:23])[C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:21])[NH:1][C:2]2[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 726563-Amino-2-pyrazinecarboxylic acid

Product 1

HCID 11438779HCID 11438779, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Aminopyrazine-2-carboxylic acid (0.7 g) in DMSO (10 ml) was treated with 3-trifluoromethylphenylisocyanate (0.9 ml), stirred at room temperature overnight and then quenched with water. A gummy residue separated. After decantation the residue was washed thoroughly with water, stirred with NaOH to basic pH, filtered and chromatographied on silica with CH2Cl2:MeOH:acetone (4:1:1) followed by CH2Cl2:MeOH:NH4OH (40:9:1) when the product started coming off the column. This gave 3-[3-(3-trifluoromethyl-phenyl)-ureido]-pyrazine-2-carboxylic acid. Mp.>300° C.

Workup

  1. customquenched with water
  2. customA gummy residue separated
  3. washAfter decantation the residue was washed thoroughly with water
  4. stirringstirred with NaOH to basic pH
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7db03acb40e147d69726ee38af4ae9f6
Source dataset
uspto-grants-2010_12
Patent number
US07851492B2

Reaction notes

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