Water → HCID 15324509, compound

HRID 1885807Notes

Reaction equation

HRID 1885807 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([SH:12])[CH:9]=[C:8]([CH3:13])[C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:32]([O:37][CH3:38])(=[O:36])[C:33]([CH3:35])=[CH2:34].O>C1(C)C=CC=CC=1>[NH2:7][C:6]1[C:8]([CH3:13])=[CH:9][C:10]([S:12][CH2:34][CH:33]([CH3:35])[C:32]([O:37][CH3:38])=[O:36])=[CH:11][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6658Methyl MethacrylateHCID 2724141Tetrabutylammonium FluorideHCID 153245012-Tert-butyl-4-mercapto-6-methylaniline

Product 1

HCID 15324509HCID 15324509, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 1.00 g (5.1 mmol) of 2-tert-butyl-4-mercapto-6-methylaniline and 0.15 g (0.5 mmol) of tetrabutylammonium fluoride in 5 mL of toluene at -5° C. is added dropwise a solution of 0.51 g (5.1 mmol) of methyl methacrylate in 5 mL of toluene. The reaction mixture is stirred for 24 hours at room temperature. The reaction mixture is then poured into 50 mL of water. The phases are separated and the organic phase is dried over anhydrous sodium sulfate. The solvent is removed in vacuo and the residue is purified by flash column chromatography (silica gel, 4:1, heptane:ethyl acetate eluent) to give 0.28 g (18%) of the title compound as a colorless liquid.

Workup

  1. customThe phases are separated
  2. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by flash column chromatography (silica gel, 4:1, heptane:ethyl acetate eluent)

Sources & evidence

ORD record
ord-79eb0a61c495409c89310733a03450e9
Source dataset
uspto-grants-1992_09
Patent number
US05145970

Reaction notes

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