Cyclohexane → 1392149-89-1

HRID 1048759Notes

Reaction equation

HRID 1048759 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH3:12])[C:8]([C:13]#[N:14])=[CH:7][C:3]=1C(O)=O.C1CCCCC1>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[CH:7][C:8]([C:13]#[N:14])=[C:9]([S:11][CH3:12])[N:10]=1

Participants

4

Reactant 2

HCID 8078CyclohexaneHCID 68276429HCID 68276429, compound

Product 1

HCID 682765271392149-89-1Yield 55.9%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 3 g (14.3 mmol) of 2-amino-5-cyano-6-(methylthio)nicotinic acid in 30 ml of diphenyl ether is stirred at 255° C. for 60 hours. After returning to room temperature, 60 ml of cyclohexane is added and the reaction medium is triturated for 30 minutes. The solid formed is filtered and then rinsed thoroughly with cyclohexane. The solid is redissolved in ethyl acetate and then the organic phase is washed with water, dried on magnesium sulfate, filtered and then evaporated to yield 1.32 g (55%) of 6-amino-2-(methylthio)nicotinonitrile in the form of a brown powder.

Workup

  1. customAfter returning to room temperature
  2. customthe reaction medium is triturated for 30 minutes
  3. customThe solid formed
  4. filtrationis filtered
  5. washrinsed thoroughly with cyclohexane
  6. dissolutionThe solid is redissolved in ethyl acetate
  7. washthe organic phase is washed with water
  8. customdried on magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-09de46960776463d86ea2cf05570c2c5
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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