4-Fluorobenzoyl chloride → HCID 67546601, compound

HRID 2356752Notes

Reaction equation

HRID 2356752 reaction equation
[NH2:1][CH:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4].[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:1][CH:2]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[C:3]([O:5][CH3:6])=[O:4])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 13848532Methyl 2-amino-2-(thiophen-2-yl)acetate

Product 1

HCID 67546601HCID 67546601, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl α-amino-2-thiophene acetate (1.48 g), 4-fluorobenzoyl chloride (1.64 g) and sodium hydrogen carbonate (2.89 g) in methylene chloride (20 ml) and water (20 ml) was stirred at room temperature overnight. The organic layer was collected, washed with water and brine, and the solvent was removed under reduced pressure. The resulting residue was triturated with ethyl acetate-hexane to obtain methyl α-(4-fluorobenzoylamino)-2-thiophene acetate (2.40 g) as colorless powder.

Workup

  1. customThe organic layer was collected
  2. washwashed with water and brine
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting residue was triturated with ethyl acetate-hexane

Sources & evidence

ORD record
ord-83396aed494243a082897438aed43be8
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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