Dimethylformamide → 1-[(2-Chlorophenyl)amino]acetone

HRID 1790044Notes

Reaction equation

HRID 1790044 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].I[CH2:10][C:11](=[O:13])[CH3:12].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:10][C:11]([CH3:12])=[O:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72402-ChloroanilineHCID 11430Potassium CarbonateHCID 763962-Propanone, 1-iodo-

Product 1

HCID 220385051-[(2-Chlorophenyl)amino]acetoneYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of chloroacetone (8.0 mL, 0.100 mol) in 100 mL acetone was added KI (33.20 g, 0.200 mol). The suspension was stirred under argon at rt for 24 h. Acetone was evaporated under reduced pressure. The residue was extracted with ether. The ethereal solution was concentrated under reduced pressure to yield iodoacetone as a brown liquid (18.00 g, 98%). A mixture of 2-chloroaniline (8.95 mL, 0.085 mol), iodoacetone (18.00 g, 0.098 mol), K2CO3 (12.35 g, 0.090 mol) and DMF (200 mL) was heated under argon for 48 h. The mixture was cooled to rt, and water was added. The mixture was extracted with ether (3×300 mL). The combined organic phases were washed with water (2×300 mL), dried over Na2SO4, and evaporated. The crude product was purified on silica gel, eluting with 1:5 EtOAc/hexanes to yield the product as a brown liquid (14.07 g, 77%), which was used in procedures similar to Examples 16 and 17.

Workup

  1. temperaturewas heated under argon for 48 h
  2. extractionThe mixture was extracted with ether (3×300 mL)
  3. washThe combined organic phases were washed with water (2×300 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude product was purified on silica gel
  7. washeluting with 1:5 EtOAc/hexanes

Sources & evidence

ORD record
ord-5ee44bbe9ff84184b47548d3f878aee1
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

Loading…