Cesium carbonate → HCID 59717866, compound

HRID 2224686Notes

Reaction equation

HRID 2224686 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:2].F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:15])[NH:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:12][CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 145174-FluorobenzonitrileHCID 2762412Ethyl N-[2-(4-hydroxyphenyl)ethyl]carbamate

Product 1

HCID 59717866HCID 59717866, compoundYield 119.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Combine 6.2 mmol of [2-(4-hydroxy-phenyl)-ethyl]-carbamic acid ethyl ester (3.6.0 g, 17.2 mmol), 4-fluorobenzonitrile (2.1 g, 17.2 mmol), cesium carbonate (11.2 g, 34.4 mmol), and N,N-dimethylformamide (80 mL), stir and heat at 85° C. for 18 hours. Cool to room temperature and evaporate on a rotary evaporator, took up residue in brine then extracted with ethyl acetate (3×50 mL). Dry the combined ethyl acetate extracts over sodium chloride/magnesium sulfate, filter, and concentrate on a rotary evaporator to yield the crude product (4.5 g). The crude product is purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes to yield {2-[4-(4-cyano-phenoxy)-phenyl]-ethyl}-carbamic acid ethyl ester (2.3 g): 1H NMR (CDCl3, 300.00 MHz): 7.66-7.60 (m, 2H), 7.31-7.24 (m, 2H), 7.07-7.00 (m, 4H), 4.72 (s, 1H), 4.16 (q, 2H, J=7.0 Hz), 3.48 (q, 2H, J=6.7 Hz), 2.86 (t, 2H, J=7.0 Hz), 1.27 (t, 3H, J=7.0 Hz). Step 3 {2-[4-(4-Acetyl-phenoxy)-phenyl]-ethyl}-carbamic acid ethyl ester

Workup

  1. temperatureCool to room temperature
  2. customevaporate on a rotary evaporator
  3. extractionthen extracted with ethyl acetate (3×50 mL)
  4. dry with materialDry the combined ethyl acetate
  5. filtrationfilter
  6. concentrationconcentrate on a rotary evaporator
  7. customto yield the crude product (4.5 g)
  8. customThe crude product is purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-5fcb0093fd274bf8b5afd58dd010a998
Source dataset
uspto-grants-2008_05
Patent number
US07378448B2

Reaction notes

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