Acetone → HCID 86632046, compound

HRID 885775Notes

Reaction equation

HRID 885775 reaction equation
[CH:1]1(O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]3=2)[C:3](O)=[C:2]1O.CC(C)=O.C([O-])([O-])=O.[K+].[K+].ClC[C:29]#[N:30]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.C(Cl)Cl>[CH:1]1([C:29]#[N:30])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]3=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 86632047HCID 86632047, compound

Product 1

HCID 86632046HCID 86632046, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
23 °C

Procedure

A 50-L, three-neck, round-bottom flask equipped with a mechanical stirrer and a thermocouple was charged with benzindene triol (1250 g), acetone (19 L) and K2CO3 (powdered) (1296 g), chloroacetonitrile (567 g), tetrabutylammonium bromide (36 g). The reaction mixture was stirred vigorously at room temperature (23±2° C.) for 16-72 h. The progress of the reaction was monitored by TLC. (methanol/CH2Cl2; 1:9 and developed by 10% ethanolic solution of PMA). After completion of reaction, the reaction mixture was filtered with/without Celite pad. The filter cake was washed with acetone (10 L). The filtrate was concentrated in vacuo at 50-55° C. to give a light-brown, viscous liquid benzindene nitrile. The crude benzindene nitrile was used as such in the next step without further purification.

Workup

  1. customAfter completion of reaction
  2. filtrationthe reaction mixture was filtered with/without Celite pad
  3. washThe filter cake was washed with acetone (10 L)
  4. concentrationThe filtrate was concentrated in vacuo at 50-55° C.

Sources & evidence

ORD record
ord-9e12cb96575846bea254e2435e2a0c47
Source dataset
uspto-grants-2012_08
Patent number
US08242305B2

Reaction notes

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