Acetone → 5-Chloro-2-methoxybenzoyl isothiocyanate

HRID 76246Notes

Reaction equation

HRID 76246 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[C:13]([S-:15])#[N:14].[K+].CC(C)=O>O1CCCC1.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([N:14]=[C:13]=[S:15])=[O:8]

Participants

6

Reactant 3

HCID 180AcetoneHCID 516872Potassium thiocyanateHCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 167716985-Chloro-2-methoxybenzoyl isothiocyanate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 1B (˜60 mmol) and KSCN (5.83 g, 60 mmol) were mixed in anhydrous tetrahydrofuran (25 mL) and anhydrous acetone (40 mL) and stirred at room temperature for 2 hrs. The reaction was diluted with diethyl ether (100 mL), filtered through celite and solvents evaporated in vacuo to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 3.95 (s, 3H), 6.95 (d, 1H), 7.52 (dd, 1H), 7.84 (d, 1H).

Workup

  1. filtrationfiltered through celite and solvents
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-daf5625425a64544816c604841c967b6
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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