Hydrochloric Acid → 2-Butyramido-5-chlorobenzamide

HRID 2225176Notes

Reaction equation

HRID 2225176 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:7][C:8]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11].[OH-].[Na+].Cl>C(OCC)(=O)C.C1COCC1>[C:1]([NH:7][C:8]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 14798Sodium HydroxideHCID 788762-Amino-5-chlorobenzamide

Product 1

HCID 210882262-Butyramido-5-chlorobenzamideYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Preparation D10, Step 1: Butyryl chloride (0.68 mL, 6.5 mmol, 1 eq) was slowly dripped into a mixture of 2-amino-5-chlorobenzamide (1.10 g, 6.5 mmol, 1 eq), 1.000N NaOH (6.50 mL, 6.5 mmol, 1 eq) and THF (enough to dissolve) at 0° C. More acid chloride and base were added to drive the reaction to completion. After 4 days ethyl acetate was added followed by 1N HCl. The layers were separated and the organic layer washed with 1N HCl (2×), saturated sodium bicarbonate (1×), and brine (1×). The organic layer was dried (MgSO4) and stripped to yield 2-butyramido-5-chlorobenzamide (1.44 g) as a white powder. Mass Spec (ESI) (M+H)+=241.0.

Workup

  1. customPreparation D10, Step 1
  2. dissolutionto dissolve) at 0° C
  3. customthe reaction to completion
  4. customThe layers were separated
  5. washthe organic layer washed with 1N HCl (2×), saturated sodium bicarbonate (1×), and brine (1×)
  6. dry with materialThe organic layer was dried (MgSO4)

Sources & evidence

ORD record
ord-32085eb15af847dca402de7448dfeb88
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

Loading…