Diethyl Ether → 6-(Methylthio)-2-oxo-benz[cd]indole-1(2H)-butanenitrile

HRID 484104Notes

Reaction equation

HRID 484104 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[C:5]3[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]=3[CH:13]=[CH:14][CH:15]=2.[H-].[Na+].BrC[CH2:20][CH2:21][CH2:22][C:23]#[N:24].CCOCC>CN(C)C=O>[CH3:1][S:2][C:3]1[C:4]2[C:5]3[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:20][CH2:21][CH2:22][C:23]#[N:24])[C:7](=[O:12])[C:6]=3[CH:13]=[CH:14][CH:15]=2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 794355-BromopentanenitrileHCID 197508246-(Methylthio)benz[cd]indol-2(1H)-one

Product 1

HCID 197508386-(Methylthio)-2-oxo-benz[cd]indole-1(2H)-butanenitrileYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 2.15 g of 6-(methylthio)-benz-[cd]indol-2(1H)-one (Example 2), 0.6 g of 60% sodium hydride in 70 ml of N,N-dimethylformamide is heated at 50° C. for 30 minutes then cooled. A solution of 2.22 g of 1-bromo-4-cyano-butane in 25 ml of N,N-dimethylformamide is added dropwise to the reaction mixture and stirring continued for 3 hours. The reaction mixture is quenched in 400 ml of ice water and extracted with (2×300 ml) of ethyl acetate. The organic layer is dried with magnesium sulfate and evaporated to afford a solid which is stirred with ether, filtered and dried to yield 2.5 g of the desired product as a solid, m.p. 120°-122° C.

Workup

  1. temperaturethen cooled
  2. customThe reaction mixture is quenched in 400 ml of ice water
  3. extractionextracted with (2×300 ml) of ethyl acetate
  4. dry with materialThe organic layer is dried with magnesium sulfate
  5. customevaporated
  6. customto afford a solid which
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-0e5ab3a3838646418302388924e10370
Source dataset
uspto-grants-1993_07
Patent number
US05229411

Reaction notes

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