Hydrochloric Acid → HCID 68491544, compound

HRID 1039157Notes

Reaction equation

HRID 1039157 reaction equation
C1N2CN3[CH2:10][N:4](C2)CN1C3.BrC[C:13]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH:23]([CH3:25])[CH3:24])=[O:14].Cl>C(Cl)(Cl)Cl>[ClH:21].[NH2:4][CH2:10][C:13]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH:23]([CH3:25])[CH3:24])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 826352472-Bromo-1-(5-chloro-2-isopropoxyphenyl)ethanone

Product 1

HCID 68491544HCID 68491544, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Add hexamethylenetetramine (36.14 g, 258 mmol) to a solution of 2-bromo-1-(5-chloro-2-isopropoxyphenyl)ethanone (75.17 g, 258 mmol) in chloroform (400 mL) at room temperature under nitrogen and stir for 2 days. Collect the solids by filtration, wash with diethyl ether, and dry overnight under reduced pressure. Suspend the solids in methanol (350 ml), cool to 0° C., and treat slowly with concentrated HCl (113 ml, 1365 mmol). Warm the mixture to room temperature and stir for 40 hours. Then heat the mixture to 55° C. for an additional 4 hours. Remove the solids by filtration, and remove the filtrate solvent under reduced pressure to provide a solid. Triturate the solid with diethyl ether. Collect the resulting material by filtration to provide 2-amino-1-(5-chloro-2-isopropoxyphenyl)ethanone hydrochloride, which is used in the next step without purification.

Workup

  1. customCollect the solids
  2. filtrationby filtration
  3. washwash with diethyl ether
  4. customdry overnight under reduced pressure
  5. temperatureWarm the mixture to room temperature
  6. stirringstir for 40 hours
  7. temperatureThen heat the mixture to 55° C. for an additional 4 hours
  8. customRemove the solids
  9. filtrationby filtration
  10. customremove the filtrate solvent under reduced pressure
  11. customto provide a solid
  12. customTriturate the solid with diethyl ether
  13. customCollect the resulting material
  14. filtrationby filtration

Sources & evidence

ORD record
ord-6b00c5dcbf5c44619ec45304bd5421b3
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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