Sodium Iodide → 4-Amino-2-(2-butanon-3-yl)oxy-5-chloro-N-[2-(dimethylamino)-ethyl]benzamide

HRID 1382969Notes

Reaction equation

HRID 1382969 reaction equation
[NH2:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[O:7])=[C:4]([OH:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH:27]([CH3:31])[C:28](=[O:30])[CH3:29]>CN(C=O)C>[NH2:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[O:7])=[C:4]([O:17][CH:27]([CH3:31])[C:28](=[O:30])[CH3:29])[CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 131422-Butanone, 3-bromo-HCID 143725824-Amino-5-chloro-N-[2-(dimethylamino)ethyl]-2-hydroxybenzamide

Product 1

HCID 143725564-Amino-2-(2-butanon-3-yl)oxy-5-chloro-N-[2-(dimethylamino)-ethyl]benzamideYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-5-chloro-N-[2-(dimethylamino)ethyl]-2-hydroxybenzamide (1.90 g, 7.37 mmoles) (prepared in Example 17), potassium carbonate (3.06 g, 2.21 mmoles), sodium iodide (1.11 g, 7.37 mmoles) and 91% 3-bromo-2-butanone (1.81 g, 12 mmoles) in DMF (30 ml) was stirred for 1.5 hours. The solvent was removed in vacuo and the residue partitioned between water and methylene chloride. The aqueous phase was extracted two more times with methylene chloride. The combined extracts were dried and concentrated in vacuo. The residue was chromatographed on a silica gel column using the solvent system of methylene chloride (99.5)-methanol (0.5)-ammonia (0.2). The appropriate fractions were combined and concentrated in vacuo to give a solid. This was recrystallized from acetonitrile to give 1.85 g of the title compound as a colorless solid, mp. 124°-125°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water and methylene chloride
  3. extractionThe aqueous phase was extracted two more times with methylene chloride
  4. customThe combined extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. concentrationconcentrated in vacuo
  8. customto give a solid
  9. customThis was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-e105ea67c5ed4fd4bed9c367cc43fef7
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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