Water → HCID 58497594, compound

HRID 1924414Notes

Reaction equation

HRID 1924414 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O.C(=O)([O-])O.[Na+].[C:19](Cl)(Cl)=[S:20]>C(Cl)(Cl)Cl>[F:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([N:1]=[C:19]=[S:20])[CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 14075433Methyl 2-amino-4-fluorobenzoate

Product 1

HCID 58497594HCID 58497594, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl 2-amino-4-fluorobenzoate (7.3 g, 43.2 mmol) was dissolved in chloro-form, followed by addition of water (150 mL) and sodium hydrogencarbonate (36.3 g, 432 mmol). Thiophosgene (3.73 mL, 47.5 mmol) was added and the mixture was stirred at RT for 2 h. Water (250 mL) was added and the mixture was extracted with DCM. The combined organics were dried (MgSO4) and evaporated to give the title compound (8.90 g, 98%).

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-8ac0ba15d3234d518f72c3515717fcb8
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

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