Potassium Carbonate → HCID 66871015, compound

HRID 535302Notes

Reaction equation

HRID 535302 reaction equation
[C:1]1([N:7]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:8]2[C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]4([C:32]5[C:31](OC)=[CH:30][CH:29]=[C:28]([N:35]([C:42]6[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=6)[C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=6)[C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:12]=3[C:11](OC)=[CH:10][CH:9]=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:42]1([N:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:28]2[C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:13]4([C:12]5[CH:11]=[CH:10][CH:9]=[C:8]([N:7]([C:1]6[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=6)[C:50]6[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=6)[C:20]=5[C:19]5[C:14]4=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:32]=3[CH:31]=[CH:30][CH:29]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 69669191HCID 69669191, compound

Product 1

HCID 66871015HCID 66871015, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

A well-stirred suspension of 35.5 g (50 mmol) of 4,4′-bis(diphenylamino)-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: 21.1 g (32.43 mmol), 65.0%, 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-04ea5ff94b24418394048e7c5ac399f1
Source dataset
uspto-grants-2014_10
Patent number
US08859111B2

Reaction notes

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