2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 11603873, compound

HRID 227684Notes

Reaction equation

HRID 227684 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][NH:10][C:9]=2[C:13]([NH2:15])=[O:14])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[N:27]=[C:28]=[O:29]>O1CCCC1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[NH:27][C:28](=[O:29])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[CH:11][NH:10][C:9]=2[C:13]([NH2:15])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 57756924HCID 57756924, compound

Product 1

HCID 11603873HCID 11603873, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To 0.055 g (0.272 mmol) of 5-(4-aminophenyl)-3H-imidazole-4-carboxamide dissolved in 4 cm3 of tetrahydrofuran is added, at a temperature in the region of 20° C. under an argon atmosphere, 0.040 cm3 (0.272 mmol) of 2-fluoro-5-trifluoromethylphenyl isocyanate. After stirring for 16 hours at a temperature in the region of 20° C., the reaction mixture is filtered through a No. 3 sinter funnel. The solid obtained is washed successively with three times 2 cm3 of tetrahydrofuran and three times 2 cm3 of pentane and is then dried under reduced pressure (2.7 kPa) to give 0.058 g of 5-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-3H-imidazole-4-carboxamide in the form of a beige-coloured solid melting at 325° C.; 1H NMR (400 MHz, DMSO d6, δ in ppm) 6.98 (broad m, 1H); 7.30 (broad m, 1H); 7.40 (m, 1H); 7.49 (partially masked m, 1H); 7.51 (d, J=8.5 Hz, 2H); 7.71 (s, 1H); 7.82 (d, J=8.5 Hz, 2H); 8.62 (dd, J=2.0 and 7.5 Hz, 1H); 9.00 (broad s, 1H); 9.37 (broad s, 1H); 12.65 (broad m, 1H); EI: m/z=407: M+; m/z=205 [C8H3NOF4]+ base peak; m/z=179 [C7H5NF4]+.

Workup

  1. additionis added, at a temperature in the region of 20° C. under an argon atmosphere
  2. filtrationthe reaction mixture is filtered through a No
  3. customThe solid obtained
  4. washis washed successively with three times 2 cm3 of tetrahydrofuran and three times 2 cm3 of pentane
  5. customis then dried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-64830aa95f3a423cab83551ec2392946
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

Loading…