Methyl 4-(chlorocarbonyl)benzoate → Methyl 4-isothiocyanatocarbonylbenzoate

HRID 1727038Notes

Reaction equation

HRID 1727038 reaction equation
[S-:1][C:2]#[N:3].[K+].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][CH:9]=1>C(#N)C>[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([N:3]=[C:2]=[S:1])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 516872Potassium thiocyanate

Product 1

HCID 59695236Methyl 4-isothiocyanatocarbonylbenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

Potassium thiocyanate (1.08 g, 1.1 eq) is added to a solution of methyl-4-chlorocarbonylbenzoate (2 g) in acetonitrile (30 ml). After stirring for 1 hour at approximately 20° C., the mixture is filtered and the filtrate is concentrated under reduced pressure at 40° C. The solid obtained is purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1) in order to produce the expected compound (2.1 g; 95% yield).

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure at 40° C
  3. customThe solid obtained
  4. customis purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1) in order

Sources & evidence

ORD record
ord-eb95d2aa433949d8b2323c914d21fa34
Source dataset
uspto-grants-2009_02
Patent number
US07495009B2

Reaction notes

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