Sodium Iodide → HCID 57488855, compound

HRID 2354370Notes

Reaction equation

HRID 2354370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:16][O:17][CH2:18][CH2:19]Br.[I-].[Na+].C(=O)(O)[O-].[Na+].FC(F)(F)C(O)=O>O.CCOCC.C(OCC)(=O)C.CC#N.O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:19][CH2:18][O:17][CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

11

Reactant 5

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 809722-Bromoethyl methyl etherHCID 516892Sodium BicarbonateHCID 2727804Ethyl 2-(3,4-dichloroanilino)acetate

Product 1

HCID 57488855HCID 57488855, compoundYield 20%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Ethyl N-(3,4-dichlorophenyl)glycinate (3.0 g, 12.1 mmol) was suspended in 2-bromoethyl methyl ether (9.09 mL, 96.7 mmol) and treated with sodium iodide (1.81 g, 12.1 mmol), sodium bicarbonate (1.02 g, 12.1 mmol), and 10 mL of DMF. The reaction was stirred for 20 hours at room temperature, but HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) indicated that only starting material (Rt=8.0 min) was present and that no reaction had taken place. The reaction was heated to 125° C. for 24 hours, after which time HPLC showed that all of the starting material was gone and that a new product peak had formed (Rt=8.7 min). The reaction mixture was poured into 200 mL of ethyl acetate, 100 mL of ether, and 250 mL of water and shaken vigorously. The layers were separated and the organic layer was washed with water (1×400 mL), dried over magnesium sulfate, filtered, and concentrated to a black oil. The oil was adsorbed onto approximately 50 g of silica gel and purified by column chromatography (300 g silica gel 40 um, gradient elution from 10% ethyl acetate/90% hexanes to 100% ethyl acetate over 110 minutes) to give ethyl N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycinate (0.73 g, 2.39 mmol, 20%) as a brown oil. MS (ES) m/e 306 [M+H]+.

Workup

  1. temperatureThe reaction was heated to 125° C. for 24 hours
  2. customhad formed (Rt=8.7 min)
  3. stirringshaken vigorously
  4. customThe layers were separated
  5. washthe organic layer was washed with water (1×400 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a black oil
  9. custompurified by column chromatography (300 g silica gel 40 um, gradient elution from 10% ethyl acetate/90% hexanes to 100% ethyl acetate over 110 minutes)

Sources & evidence

ORD record
ord-f515c1f2fcc849c7828ac8d56816acfc
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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