Sulfuric Acid → HCID 178423920, compound

HRID 1425650Notes

Reaction equation

HRID 1425650 reaction equation
[C:1]([C:3]1[C:4]([SH:11])=[N:5][C:6]([CH3:10])=[CH:7][C:8]=1[CH3:9])#[N:2].[OH:12]S(O)(=O)=O>>[CH3:9][C:8]1[CH:7]=[C:6]([CH3:10])[N:5]=[C:4]2[S:11][N:2]=[C:1]([OH:12])[C:3]=12

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 178425247HCID 178425247, compound

Product 1

HCID 178423920HCID 178423920, compound

Conditions

Temperature
105 °C

Procedure

3-Cyano-4,6-dimethyl-2-mercaptopyridine (4.7 g, 28.6 mmol) is dissolved in H2SO4(60 ml, 98%) and then stirred at 105° C. for 3 h. The reaction is monitored by HPLC-MS. The reaction solution is cooled to 25° C. and then poured onto ice. The product eventually (15 min) precipitates out as a voluminous solid and is filtered off with suction and washed with H2O. The residue is taken up with aqueous Na2CO3 solution (pH 8-9) and the product is extracted with EtOAc. The solvent is distilled off under reduced pressure and the residue (white solid) is dried (Na2SO4).

Workup

  1. temperatureThe reaction solution is cooled to 25° C.
  2. additionpoured onto ice
  3. customThe product eventually (15 min) precipitates out as a voluminous solid
  4. filtrationis filtered off with suction
  5. washwashed with H2O
  6. extractionthe product is extracted with EtOAc
  7. distillationThe solvent is distilled off under reduced pressure
  8. dry with materialthe residue (white solid) is dried (Na2SO4)

Sources & evidence

ORD record
ord-fcbcb9f572954bcdaf333b46fada9c2b
Source dataset
uspto-grants-2015_01
Patent number
US08933024B2

Reaction notes

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