Hydrochloric Acid → HCID 178447852, compound

HRID 1589747Notes

Reaction equation

HRID 1589747 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C@H:20]4[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:29]([Cu])#[N:30].CN1C(=O)CCC1.Cl>O>[C:29]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C@H:20]4[CH2:21][CH2:22][C@H:23]([CH2:26][CH2:27][CH3:28])[CH2:24][CH2:25]4)=[CH:16][CH:15]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1)#[N:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 178418546HCID 178418546, compoundHCID 178447850HCID 178447850, compound

Product 1

HCID 178447852HCID 178447852, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3.3 g of 2-(4'-bromophenyl)-5-[4'-(trans-4"-propylcyclohexyl)phenyl]pyrimidine and 0.9 g (0.01 mol) of CuCN were added to 30 cm3 of NMP and the solution was refluxed for 2 hours using a mantle heater. The solution was cooled to 60° C. and added to a solution of 4.4 g of FeCl3.6H2O, 1.3 cm3 of concentrated hydrochloric acid and 6 cm3 of water. The resulting solution was heated on a warm water bath at a temperature of 60° C. for one hour. The crystals deposited were filtered out, washed with water and treated through a silica gel column using chloroform as the solvent. The chloroform was distilled off and the residue was recrystallized from a mixture of acetone and chloroform to yield 2.2 g (0.006 mol) of 2-(4'-cyanophenyl)-5-[4'-(trans-4"-propylcyclohexyl) phenyl] pyrimidine. The phase transition temperature of this compound, measured by DSC, was: ##STR28## wherein C is the crystal phase, N is the nematic phase and I is the isotropic liquid phase.

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. temperatureThe resulting solution was heated on a warm water bath at a temperature of 60° C. for one hour
  3. filtrationThe crystals deposited were filtered out
  4. washwashed with water
  5. additiontreated through a silica gel column
  6. distillationThe chloroform was distilled off
  7. customthe residue was recrystallized from a mixture of acetone and chloroform

Sources & evidence

ORD record
ord-0877a1c0198c450689437557e2e6876e
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

Loading…