Potassium Hydroxide → HCID 10705031, compound

HRID 1740497Notes

Reaction equation

HRID 1740497 reaction equation
[OH-].[K+].[N+]([C:6]1[CH:7]=[C:8]([O:14][CH3:15])[CH:9]=[CH:10][C:11]=1[C:12]#[N:13])([O-])=O.[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18]>O>[NH2:13][C:12]1[C:11]2[CH:10]=[CH:9][C:8]([O:14][CH3:15])=[CH:7][C:6]=2[S:18][C:17]=1[C:16]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 16907Methyl ThioglycolateHCID 2886654-Methoxy-2-nitrobenzonitrile

Product 1

HCID 10705031HCID 10705031, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 20.3 g (0.363 mol) of potassium hydroxide in 100 ml of water is added to a mixture of 36.3 g (0.204 mol) of 3-nitro-4-cyanoanisole and 26 g (0.245 mol) of methyl thioglycolate in 400 ml of N,N-d-methylformamide, the temperature being maintained at 0° C. The mixture is left stirring at 0° C. for 20 min and is then poured into a mixture of water and ice. The precipitate is then filtered off, rinsed with water and dried. The product is dissolved in a mixture of dichloromethane and tetrahydrofuran, the organic phase is then dried over sodium sulphate and concentrated under reduced pressure and the residue is triturated in dichloromethane. 26.2 g of product are thus obtained in the form of a light-beige powder.

Workup

  1. waitThe mixture is left
  2. filtrationThe precipitate is then filtered off
  3. washrinsed with water
  4. customdried
  5. dissolutionThe product is dissolved in a mixture of dichloromethane and tetrahydrofuran
  6. dry with materialthe organic phase is then dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue is triturated in dichloromethane

Sources & evidence

ORD record
ord-45f9dc8849b641c59b7ac68f91570867
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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