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

HRID 1784262Notes

Reaction equation

HRID 1784262 reaction equation
[S-:1][C:2]#[N:3].[K+].Cl[C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=[O:7]>C(#N)C>[N:3]([C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=[O:7])=[C:2]=[S: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) 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-ffcd27c13af2459bb65a0f9ff902e5f1
Source dataset
uspto-grants-2009_03
Patent number
US07501524B2

Reaction notes

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