Acetone → HCID 86632046, compound

HRID 404992Notes

Reaction equation

HRID 404992 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-36fb88704fa647b1b6014379f5400459
Source dataset
uspto-grants-2014_06
Patent number
US08748657B2

Reaction notes

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