Tetrahydrofuran → 2-Butyramido-5-chlorobenzamide

HRID 351411

Reaction equation

HRID 351411 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH-].[Na+].[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1.C(Cl)(=O)CCC>C(OCC)(=O)C>[C:16]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])(=[O:17])[CH2:15][CH2:14][CH3:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8855Butyryl chlorideHCID 14798Sodium HydroxideHCID 788762-Amino-5-chlorobenzamide

Product 1

HCID 210882262-Butyramido-5-chlorobenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-5-chlorobenzamide (1.10 g, 6.5 mmol, 1 eq.), 1.000 N NaOH (6.50 mL, 6.5 mmol, 1 eq.) and THF (20 mL) were mixed and stirred at 0° C. To this mixture was added butyryl chloride dropwise (0.68 mL, 6.50 mmol, 1 eq.). More acid chloride and base were added to drive reaction to completion. The reaction was allowed to warm to rt. After 4 days the reaction was worked up by adding ethyl acetate, washing with 1 N HCl (3×), saturated sodium bicarbonate (1×), and brine (1×). The organic layer was dried and stripped to yield 1.44 g of a white powder as product. LCMS detects (M+H)+=241.0.

Workup

  1. customreaction to completion
  2. temperatureto warm to rt
  3. washwashing with 1 N HCl (3×), saturated sodium bicarbonate (1×), and brine (1×)
  4. customThe organic layer was dried

Sources & evidence

ORD record
ord-ca406a373050475d8dfdff6ea911caab
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Linked notes

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