Bromotrimethylsilane → HCID 21930307, compound

HRID 1243651Notes

Reaction equation

HRID 1243651 reaction equation
C([O:3][P:4]([C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)=[O:18])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>C(Cl)(Cl)Cl>[P:4]([C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=1)=[O:18])([OH:6])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 21065007HCID 21065007, compound

Product 1

HCID 21930307HCID 21930307, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a 40 mL vial containing a stirring bar, 1-(2-Diethylphosphono-4-bromophenyl)-3-(3-trifluoromethylphenyl)urea (1.2 g, 2.42 mmol) was added along with 15 mL of CHCl3. This was cooled in an ice bath and then bromotrimethylsilane (5.0 g, 32.7 mmol) was added slowly under N2 while stirring. The bath was removed after the addition and then the vial was sealed and heated at 40° C. for 2 days. The resulting solution was cooled in an ice bath and water was added dropwise (5 mL) followed by 10 mL of isopropanol. After 10 minutes the bath was removed and the reaction was stirred at room temperature for one day. The mixture was then diluted with 50 mL water and concentrated until a precipitate formed. The precipitate was filtered and then recrystallized from ethyl acetate to give 750 mg of 1-(2-Phosphono-4-bromophenyl)-3-(3-trifluoromethylphenyl)urea as a white solid. 1H-NMR (400 MHz, DMSO-D6): δ=7.27 (d, 8.0 Hz, 1H, CHCHCCF3), 7.43 (m, 1H, CHCHCCF3), 7.60 (m, 2H, CHCBrCH), 7.70 (dd, 15 Hz, 2H2, 1H, BsCCHCP) 7.90 (s, 1H, CHCF3), 8.05 (m, 1H). 31P (400 Mz, CDCl3) δ=13.41 (s).

Workup

  1. additionTo a 40 mL vial containing a stirring bar
  2. temperatureThis was cooled in an ice bath
  3. customThe bath was removed
  4. additionafter the addition
  5. customthe vial was sealed
  6. temperatureThe resulting solution was cooled in an ice bath
  7. additionwater was added dropwise (5 mL)
  8. customAfter 10 minutes the bath was removed
  9. stirringthe reaction was stirred at room temperature for one day
  10. additionThe mixture was then diluted with 50 mL water
  11. concentrationconcentrated until a precipitate
  12. customformed
  13. filtrationThe precipitate was filtered
  14. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-45dd2957367b4298be04394f3d6e9098
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

Loading…