HCID 178527052, compound → HCID 178510800, compound

HRID 2111940Notes

Reaction equation

HRID 2111940 reaction equation
C([NH:14][CH:15]([PH:23](=[O:25])[OH:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C1C=CC=CC=1)C1C=CC=CC=1>Br>[NH2:14][CH:15]([PH:23](=[O:24])[OH:25])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 178527052HCID 178527052, compound

Product 1

HCID 178510800HCID 178510800, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

181.1 g of the compound of Step A above in 500 ml of hydrobromic acid are heated at 110-120° C. for 2 hours. The mixture is then concentrated under reduced pressure, and the residue is diluted with water and extracted with diethyl ether. The aqueous phase is concentrated and 600 ml of absolute ethanol are added to the residue. 60 ml of previously cooled propylene oxide are slowly added to the reaction mixture, which is held at 0° C. The expected product which precipitates out on cooling is filtered off, washed with diethyl ether and then dried.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with diethyl ether
  4. concentrationThe aqueous phase is concentrated
  5. addition600 ml of absolute ethanol are added to the residue
  6. addition60 ml of previously cooled propylene oxide are slowly added to the reaction mixture, which
  7. customis held at 0° C
  8. customThe expected product which precipitates out
  9. temperatureon cooling
  10. filtrationis filtered off
  11. washwashed with diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-596da9a3a112428bb0934e762e35ee03
Source dataset
uspto-grants-2009_04
Patent number
US07521469B2

Reaction notes

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