Potassium Carbonate → HCID 66871763, compound

HRID 535303Notes

Reaction equation

HRID 535303 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([C:19]3[C:31]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]5([C:43]6[C:42](OC)=[CH:41][CH:40]=[C:39]([C:46]7[N:51]=[C:50]([C:52]8[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=8)[N:49]=[C:48]([C:58]8[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=8)[N:47]=7)[C:38]=6[C:37]6[C:32]5=[CH:33][CH:34]=[CH:35][CH:36]=6)[C:23]=4[C:22](OC)=[CH:21][CH:20]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N2C(Cl)=NN=N2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:58]1([C:48]2[N:49]=[C:50]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[N:51]=[C:46]([C:39]3[C:38]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:24]5([C:23]6[CH:22]=[CH:21][CH:20]=[C:19]([C:9]7[N:8]=[C:7]([C:1]8[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=8)[N:12]=[C:11]([C:13]8[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=8)[N:10]=7)[C:31]=6[C:30]6[C:25]5=[CH:26][CH:27]=[CH:28][CH:29]=6)[C:43]=4[CH:42]=[CH:41][CH:40]=3)[N:47]=2)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 69671495HCID 69671495, compound

Product 1

HCID 66871763HCID 66871763, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

A well-stirred suspension of 41.9 g (50 mmol) of 4,4′-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-1,1′-dimethoxy-9,9′-spirobifluorene, 18.1 g (100 mmol) of 1-phenyl-5-chlorotetrazole and 27.6 g (200 mmol) of K2CO3 is heated under reflux for 18 h in 250 ml of acetone. After cooling, the precipitated solid is filtered off with suction and dried. The solid is dissolved in 200 ml of toluene, 6 g of Pd/C (5%) are added, and the mixture is stirred at 40° C. for 8 h under a hydrogen atmosphere. After removal of the solvent, the residue is washed three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol and subsequently recrystallised three times from DMF (about 10 ml/g). Yield: 25.6 g (32.96 mmol), 66.0%, purity: 99.9% (HPLC).

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. filtrationthe precipitated solid is filtered off with suction
  4. customdried
  5. dissolutionThe solid is dissolved in 200 ml of toluene
  6. addition6 g of Pd/C (5%) are added
  7. customAfter removal of the solvent
  8. washthe residue is washed three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  9. customsubsequently recrystallised three times from DMF (about 10 ml/g)

Sources & evidence

ORD record
ord-5b47d4efb20a41c1a30908a1c56ba9a0
Source dataset
uspto-grants-2014_10
Patent number
US08859111B2

Reaction notes

Loading…