Methyl Thioglycolate → HCID 9928750, compound

HRID 1898945Notes

Reaction equation

HRID 1898945 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([O:17][CH3:18])(=[O:16])[CH2:14][SH:15].[CH3:19][N:20]([CH3:38])[C:21]1[CH:37]=[CH:36][C:24]([CH:25](O)[C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:34][N:32]([CH3:33])[C:29]1[CH:28]=[CH:27][C:26]([CH:25]([C:24]2[CH:36]=[CH:37][C:21]([N:20]([CH3:38])[CH3:19])=[CH:22][CH:23]=2)[S:15][CH2:14][C:13]([O:17][CH3:18])=[O:16])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 16907Methyl ThioglycolateHCID 927424,4'-Bis(dimethylamino)benzhydrolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 9928750HCID 9928750, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of ρ-toluenesulfonic acid monohydrate (1.50 g, 7.89 mmol) and activated 3 Å molecular sieves (300-500 mg) in 7 mL of toluene is stirred for 15 minutes. Methyl thioglycolate (410 mg, 3.86 mmol) is then added followed by 4,4'-bis(dimethyamino)benzhydrol (Aldrich) (950 mg, 3.51 mmol) and stirred for 1 hour. The reaction is diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, brine and dried over magnesium sulfate. Chromatography on silica gel, eluting with a 1:4 mixture of ethyl acetate: hexane, provides methyl [[bis-(4-dimethylaminophenyl)methyl]thio]acetate as a greenish yellow solid in 53% yield.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. washChromatography on silica gel, eluting with a 1:4 mixture of ethyl acetate

Sources & evidence

ORD record
ord-94b8def57532464ebf920d2cd689aa0b
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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