Methyl Acrylate → Methyl 3-(4-Amino-3-tert-butyl-5-methylphenylthio)propionate

HRID 1109668

Reaction equation

HRID 1109668 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].C(N(CC)CC)C.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23]>C1(C)C=CC=CC=1>[NH2:7][C:6]1[C:8]([CH3:13])=[CH:9][C:10]([S:12][CH2:23][CH2:22][C:21]([O:25][CH3:26])=[O:24])=[CH:11][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 153245012-Tert-butyl-4-mercapto-6-methylaniline

Product 1

HCID 15324502Methyl 3-(4-Amino-3-tert-butyl-5-methylphenylthio)propionateYield 66.2%

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 0.05 g (0.5 mmol) of triethylamine in 5 mL of toluene at -5° C. is added dropwise a solution of 0.44 g (5.1 mmol) of methyl acrylate in 5 mL of toluene. The reaction mixture is stirred for 24 hrs at room temperature. The solvent is removed in vacuo and the crude product is purified by flash column chromatography (silica gel, 95:5, heptane:ethyl acetate eluent) to give 0.95 g (66%) of the title compound as a colorless liquid.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude product is purified by flash column chromatography (silica gel, 95:5, heptane:ethyl acetate eluent)

Sources & evidence

ORD record
ord-2cc6bd1acc094a6ea7230d1d66f53bb5
Source dataset
uspto-grants-1994_06
Patent number
US05321067

Linked notes

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