Potassium Hydroxide → HCID 15421643, compound

HRID 2275820Notes

Reaction equation

HRID 2275820 reaction equation
Br[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=[O:5].O1CCOCCOCCOCCOCCOCC1.[OH-].[K+].[Cl-].[NH4+]>ClCCl>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([N:6]2[CH2:2][CH2:3][C:4]2=[O:5])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 85797500HCID 85797500, compound

Product 1

HCID 15421643HCID 15421643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20.30 g of 3-bromo-N-[4-(trifluoromethyl)phenyl]propanamide (Example 153A, 66.16 mmol, 1 equivalent) were initially charged in 161 ml of dichloromethane, 18.54 g of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6, 70.13 mmol, 1.06 equivalents) and 3.86 g of potassium hydroxide (68.81 mmol, 1.04 equivalents) were added and the mixture was stirred at RT overnight. Saturated aqueous ammonium chloride solution was added and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and filtered and the filtrate was concentrated. This gave 25.0 g (86% of theory; purity about 49%) of the title compound which was reacted further without purification.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThis gave 25.0 g (86% of theory; purity about 49%) of the title compound which was reacted further without purification

Sources & evidence

ORD record
ord-ab25ab182fdd45f485a4f7b332808c1d
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…