Water → 5-tert-Butyl4-dimethylthiocarbamoyloxy-2-methyl-benzoic acid methyl ester

HRID 356498Notes

Reaction equation

HRID 356498 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]([OH:14])=[CH:6][C:5]=1[CH3:15].[H-].[Na+].[CH3:19][N:20]([CH3:24])[C:21](Cl)=[S:22].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([CH3:11])([CH3:12])[CH3:13])[C:7]([O:14][C:21](=[S:22])[N:20]([CH3:24])[CH3:19])=[CH:6][C:5]=1[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 10632819Methyl 5-(tert-butyl)-4-hydroxy-2-methylbenzoate

Product 1

HCID 538656495-tert-Butyl4-dimethylthiocarbamoyloxy-2-methyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-tert-butyl-4-hydroxy-2-methylbenzoic acid methyl ester from Example BBB (15.1 g, 68 mmol) in DMF (150 mL) was added NaH (3.3 g of a 60% dispersion, 82 mmol), and the mixture was stirred at room temperature for 1 hour. N,N-Dimethylthiocarbamoyl chloride (10.1 g, 82 mmol) was added all at once; the reaction mixture was stirred at 55° C. for 36 hours and then cooled to room temperature. H2O (200 mL) was added, and the solution was extracted with EtOAc. The combined extracts were washed with 1N NaOH, 1N HCl, and brine. The organic phase was dried (MgSO4) and concentrated. The residue was chromatographed on silica gel, eluting with 6:1 hexane:EtOAc, to give the title compound. 1H NMR (CDCl3) δ 1.37 (s, 9 H), 2.55 (s, 3 H), 3.39 (s, 3 H), 3.49 (s, 3 H), 3.89 (s, 3 H), 6.90 (s, 1 H), 8.01 (s, 1 H).

Workup

  1. stirringthe reaction mixture was stirred at 55° C. for 36 hours
  2. temperaturecooled to room temperature
  3. extractionthe solution was extracted with EtOAc
  4. washThe combined extracts were washed with 1N NaOH, 1N HCl, and brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 6:1 hexane

Sources & evidence

ORD record
ord-d9c08af142a24b23b301b8b6b49be27b
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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