4-Methoxybenzonitrile → HCID 22503375, compound

HRID 1006949Notes

Reaction equation

HRID 1006949 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[CH3:10])=[O:4].[Li]CCCC.C1COCC1.C(#N)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1>C1COCC1>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:1]2[NH:2][C:3](=[O:4])[C:5]3[CH:9]=[CH:8][S:7][C:6]=3[CH:10]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 701294-MethoxybenzonitrileHCID 22503091n-Methyl-2-methylthiophene-3-carboxamideHCID 178420697HCID 178420697, compound

Product 1

HCID 22503375HCID 22503375, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of N-methyl-2-methylthiophene-3-carboxamide (36.0 g) in THF (500 ml) was added dropwise 2.5M n-BuLi/THF solution (200 ml) at −70° C. The reaction solution was stirred at −70° C. for 2 hr, followed by the addition of anisonitrile (31.0 g) at once. After the dry ice/acetone bath was removed, the reaction mixture was back to room temperature. Three hours later, an aqueous solution of saturated ammonium chloride and ether were added thereto, and then the mixture was further stirred for 1 hr. The resulting white precipitates were collected by filtration, washed with water, ether and n-hexane in this order, and then dried, to give the title compound (17.9 g, yield; 30%).

Workup

  1. customAfter the dry ice/acetone bath was removed
  2. customwas back to room temperature
  3. additionThree hours later, an aqueous solution of saturated ammonium chloride and ether were added
  4. stirringthe mixture was further stirred for 1 hr
  5. customThe resulting white precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water, ether and n-hexane in this order
  8. customdried

Sources & evidence

ORD record
ord-68edf2d14c8e46e693393f712a601978
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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