Sulfuric Acid → HCID 59186085, compound

HRID 1671362Notes

Reaction equation

HRID 1671362 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].[CH3:5][C:6]1[CH:13]=[C:12]([S:14][CH3:15])[CH:11]=[CH:10][C:7]=1[C:8]#N.[OH:16]S(O)(=O)=O>C1(C)C=CC=CC=1>[CH3:5][C:6]1[CH:13]=[C:12]([S:14][CH3:15])[CH:11]=[CH:10][C:7]=1[C:8](=[O:16])[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 59186105HCID 59186105, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 59186085HCID 59186085, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of EtMgBr (11.90 ml, 35.72 mmol) in toluene (40 ml) at 0° C. is added 2-Methyl-4-methylsulfanyl-benzonitrile (2.43 g, 14.89 mmol) in toluene dropwise over 30 mins. The reaction is then left to reach RT overnight with stirring. After this time, the contents are poured into ice, conc. H2SO4 (3 ml) is added and the contents are vigorously stirred for 4 hrs at RT. The misture is extracted into EtOAc, washed with H2O, brine, dried (MgSO4) and concentrated in vacuo to give a yellow solid; MS m/z=195.1 [M+H]+; H NMR 400.13 MHz (CDCl3) −7.09 (2H, m), 2.41 (2H, q), 2.52 (6H, s), 1.20 (3H, t).

Workup

  1. waitThe reaction is then left
  2. additionis added
  3. stirringthe contents are vigorously stirred for 4 hrs at RT
  4. extractionThe misture is extracted into EtOAc
  5. washwashed with H2O, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a yellow solid

Sources & evidence

ORD record
ord-56514b2c8b4c48e6aca482ab58619ecf
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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