3,5-Bis(trifluoromethyl)phenyl isocyanate → HCID 21930328, compound

HRID 1243650Notes

Reaction equation

HRID 1243650 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N:13]=[C:14]=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:18]([O:20][P:21]([C:26]1[CH:32]=[C:31]([Br:33])[CH:30]=[CH:29][C:27]=1[NH2:28])([O:23][CH2:24][CH3:25])=[O:22])[CH3:19]>>[CH2:18]([O:20][P:21]([C:26]1[CH:32]=[C:31]([Br:33])[CH:30]=[CH:29][C:27]=1[NH:28][C:14]([NH:13][C:5]1[CH:4]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=1)=[O:15])([O:23][CH2:24][CH3:25])=[O:22])[CH3:19]

Participants

3

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 21065035HCID 21065035, compound

Product 1

HCID 21930328HCID 21930328, compound

Conditions

Temperature
65 °C

Procedure

To an oven dried 30 mL vial containing a stirring bar 2 mL of pyridine was added followed by 3,5-bistrifluorometylphenylisocyanate (35 mg, 0.125) and 2-Diethylphosphono-4-bromoaniline (32 mg, 0.104 mmol). The resulting solution was stirred at 65° C. for 3 hours. Pyridine was removed by rotary evaporation and then the product was purified by silica column chromatography using mixtures of EtOAc and hexanes to give 1-(2-diethylphosphono-4-bromophenyl)-3-(3,5-bistrifluoromethylphenyl)urea. 1H-NMR (400 MHz, CDCl3): δ=1.32 (t, 6.8 Hz, 6H CH3), 4.10 (m, 4H, CH2), 7.52 (s, 1H, CCF3CHCCF3), 7,64 (m, 2H, CHCBRCH), 8.03 (s, 2H, CCF3CHCNH), 8.30 (m, 1H, CPCNCH), 8.62 (s, 1H, NH), 9.82 (s, 1H, PCCNH). 31P (400 Mz, CDCl3) δ=18.19 (s)

Workup

  1. customTo an oven dried 30 mL
  2. additionvial containing a stirring bar 2 mL of pyridine
  3. additionwas added
  4. customPyridine was removed by rotary evaporation
  5. customthe product was purified by silica column chromatography

Sources & evidence

ORD record
ord-03891c3b3c8f4186bd0b776666a2fd4d
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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