Hydrochloric Acid → Methyl 4-(aminocarbonothioyl)-2-fluorobenzoate

HRID 589933Notes

Reaction equation

HRID 589933 reaction equation
O.[SH2:2].[Na].[C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([F:16])[CH:7]=1)#[N:5].O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].Cl>O.CN(C)C=O>[NH2:5][C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([F:16])[CH:7]=1)=[S:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24644Magnesium chloride hexahydrateHCID 15278726Methyl 4-cyano-2-fluorobenzoateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 117701144Methyl 4-(aminocarbonothioyl)-2-fluorobenzoateYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A sodium hydrogensulfide hydrate (9.22 g, 0.165 mol) was added to an N,N-dimethylformamide (74 mL) suspension of methyl 4-cyano-2-fluorobenzoate (WO 2010/115751) (7.37 g, 41.1 mmol) and magnesium chloride hexahydrate (10.0 g, 49.4 mmol) at room temperature. The mixture was stirred at room temperature for 4 hours. Subsequently, water (148 mL) was added to the reaction mixture, and the precipitated solid was filtered. The solid thus obtained was added to 1 N aqueous hydrochloric acid solution (148 mL), and the mixture was stirred for 20 minutes. The solid in the reaction mixture was filtered to give the title compound (7.63 g, yield: 87%).

Workup

  1. filtrationthe precipitated solid was filtered
  2. customThe solid thus obtained
  3. stirringthe mixture was stirred for 20 minutes
  4. filtrationThe solid in the reaction mixture was filtered

Sources & evidence

ORD record
ord-53f9087416ab4fd68d55a2738759e3b2
Source dataset
uspto-grants-2016_01
Patent number
US09233958B2

Reaction notes

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