Potassium Hydroxide → HCID 178515968, compound

HRID 1170048Notes

Reaction equation

HRID 1170048 reaction equation
C[O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=2)[CH2:12][CH:13]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([O:42]C)[N:37]=3)[CH:31]=2)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27]C)[N:22]=3)[CH:16]=2)[CH:6]=[CH:5][CH:4]=1.Cl.[NH+]1C=CC=CC=1.[OH-].[K+]>O>[OH:27][C:23]1[N:22]=[C:21]([C:17]2[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=2)[CH2:14][CH:13]([CH2:12][C:11]2[CH:44]=[CH:45][CH:46]=[C:9]([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([OH:2])[N:8]=3)[CH:10]=2)[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([OH:42])[N:37]=3)[CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21584435Pyridinium hydrochlorideHCID 68525269HCID 68525269, compound

Product 1

HCID 178515968HCID 178515968, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 4.9 g (8.0 mmol) of tris(3-(6-methoxy-2-pyridyl)benzyl)methane and 7.4 g (64 mmol) of pyridinium hydrochloride was heated at 190° C. for 3 h. After cooling, the mixture was taken up in 200 ml of water and adjusted to pH=7.7 using 1N potassium hydroxide solution. The aqueous phase was extracted five times with 200 ml of dichloromethane. The organic phase was dried over magnesium sulfate and filtered through a short frit with silica gel. After removal of the solvent, the residue was recrystallised from tert-butyl methyl ether:n-heptane (1:2). The yield, with a purity of about 97%, was 3.8 g (6.7 mmol), corresponding to 83.8% of theory.

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous phase was extracted five times with 200 ml of dichloromethane
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered through a short frit with silica gel
  5. customAfter removal of the solvent
  6. customthe residue was recrystallised from tert-butyl methyl ether:n-heptane (1:2)

Sources & evidence

ORD record
ord-4d43dc563e4049a5ac812b6778103b8e
Source dataset
uspto-grants-2010_11
Patent number
US07825249B2

Reaction notes

Loading…