Pivaloyl chloride → Isopropyl 2-chloro-5-((2,2-dimethylpropanoyl)amino)-4-fluorobenzoate

HRID 326348Notes

Reaction equation

HRID 326348 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[C:10]([F:22])=[CH:11][C:12]([Cl:21])=[C:13]([CH:20]=1)[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15]>C(C(C)=O)C>[Cl:21][C:12]1[CH:11]=[C:10]([F:22])[C:9]([NH:8][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[CH:20][C:13]=1[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 13519894Propan-2-yl 5-amino-2-chloro-4-fluorobenzoate

Product 1

HCID 361505Isopropyl 2-chloro-5-((2,2-dimethylpropanoyl)amino)-4-fluorobenzoateYield 79%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of trimethylacetyl chloride (2.53 g, 0.021 mole) and 1-methylethyl 5-amino-2-chloro-4-fluorobenzoate (4.62 g, 0.020 mole) in methyl ethyl ketone was stirred at room temperature for 16 hours and then refluxed for 2 hours. The solvent was removed and the residue triturated with diethyl ether to give a tan solid, m.p. 81°-83° C. (5.0 g, 79% yield).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solvent was removed
  3. customthe residue triturated with diethyl ether
  4. customto give a tan solid, m.p. 81°-83° C. (5.0 g, 79% yield)

Sources & evidence

ORD record
ord-d8500ae06dc245d6828ac67971ac12b9
Source dataset
uspto-grants-1993_12
Patent number
US05268389

Reaction notes

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