Ammonia → HCID 57825027, compound

HRID 1668699Notes

Reaction equation

HRID 1668699 reaction equation
II.[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[CH2:11])[CH:5]=1.N.[NH2:21][C:22]([NH2:24])=[O:23]>C(OCC)(=O)C.C(#N)C.[Ag]OC#N>[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[CH2:11][O:23][C:22]([NH2:24])=[N:21]2)[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 1176UreaHCID 57825182HCID 57825182, compound

Product 1

HCID 57825027HCID 57825027, compound

Reagents, catalysts & solvents 3

HCID 178513473HCID 178513473, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of iodine (1.65 g, 6.7 mmol) in ethyl acetate (25 mL) was added dropwise over 25 min to a mixture of 1-bromo-3-(1-(3-methoxy-phenyl)-vinyl)-benzene (1.75 g, 6.1 mmol) and silver cyanate in acetonitrile (30 mL) and ethyl acetate (15 mL), cooled in an ice bath. After complete addition, the reaction suspension was stirred for another 15 min at room temperature when TLC indicated the complete conversion of starting material. The reaction mixture was filtered, and the filtrate concentrated to give a dark grey oil. 25 mL of aqueous ammonia (25%) was added to the oil, and the mixture was stirred and warmed to 70° C. for 30 min, then kept at room temperature overnight. LC-MS at this point indicated complete conversion of the intermediate urea to the desired aminoxazoline. The reaction suspension was filtered, the solid was refluxed in toluene (20 mL) for 10 min, filtered hot (to remove residual, undissolved silver iodide), and the filtrate was left to cool to room temperature, followed by 1 h at −10° C. The pale-yellow crystalline solid was filtered off and dried at the rotary evaporator to dive 4-(3-bromo-phenyl)-4-(3-methoxy-phenyl)-4,5-dihydro-oxazol-2-ylamine (1.2 g, 57%).

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter complete addition
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated
  5. customto give a dark grey oil
  6. stirringthe mixture was stirred
  7. temperaturewarmed to 70° C. for 30 min
  8. waitkept at room temperature overnight
  9. filtrationThe reaction suspension was filtered
  10. temperaturethe solid was refluxed in toluene (20 mL) for 10 min
  11. filtrationfiltered hot
  12. custom(to remove residual, undissolved silver iodide)
  13. waitthe filtrate was left
  14. temperatureto cool to room temperature
  15. waitfollowed by 1 h at −10° C
  16. filtrationThe pale-yellow crystalline solid was filtered off
  17. customdried at the rotary evaporator

Sources & evidence

ORD record
ord-d6b042d9966241209a64fb82c993924d
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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