Triethylamine hydrochloride → Methyl 4-carbamothioyl-3-methylbenzoate

HRID 2093155Notes

Reaction equation

HRID 2093155 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH3:13])#[N:2].[SH2:14].[Na].Cl.C(N(CC)CC)C>O1CCOCC1.O>[NH2:2][C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH3:13])=[S:14]

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 19969932Methyl 4-cyano-3-methylbenzoateHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 53832239Methyl 4-carbamothioyl-3-methylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of methyl 4-cyano-3-methylbenzoate (36 mg, 0.205 mmol) in 1,4-dioxane (0.5 mL) and water (0.500 mL), was added sodium hydrogen sulfide (0.019 mL, 0.616 mmol) and triethylamine hydrochloride (170 mg, 1.233 mmol). The reaction mixture was heated at 55° C. overnight. The reaction was allowed to cool and water was added. The mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and the solvent was evaporated in vacuo to give the product as a yellow solid. LCMS calc.=210.1; found=210.2 (M+1)+. 1H NMR (500 MHz, CDCl3) 7.86 (s, 1 H); 7.84 (d, J=8.1 Hz, 1 H); 7.42 (d, J=7.9 Hz, 1 H); 7.16 (s, 2 H); 3.93 (s, 3 H); 2.51 (s, 3 H).

Workup

  1. temperatureto cool
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3991a109155b4e399845a93c6e86aa2f
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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