Hydrochloric Acid → HCID 19040952, compound

HRID 1683824Notes

Reaction equation

HRID 1683824 reaction equation
C(C1C=C[C:6]([O:7]CCCCCOC2C=CC(C(N(C(C)C)C(C)C)=O)=C(O)C=2)=[CH:5]C=1)#N.[H-].[Na+].BrCC(OCC)=O.[C:41]([C:43]1[CH:77]=[CH:76][C:46]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][O:53][C:54]2[CH:55]=[CH:56][C:57]([C:67]([N:69]([CH:73]([CH3:75])[CH3:74])[CH:70]([CH3:72])[CH3:71])=[O:68])=[C:58]([CH:66]=2)[O:59][CH2:60][C:61]([O:63][CH2:64][CH3:65])=[O:62])=[CH:45][CH:44]=1)#[N:42].[ClH:78]>CN(C)C=O.C(O)C>[ClH:78].[CH2:64]([O:63][C:61]([CH2:60][O:59][C:58]1[CH:66]=[C:54]([CH:55]=[CH:56][C:57]=1[C:67]([N:69]([CH:73]([CH3:75])[CH3:74])[CH:70]([CH3:71])[CH3:72])=[O:68])[O:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][O:47][C:46]1[CH:45]=[CH:44][C:43]([C:41](=[NH:42])[O:7][CH2:6][CH3:5])=[CH:77][CH:76]=1)=[O:62])[CH3:65]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 19040962HCID 19040962, compoundHCID 19040982HCID 19040982, compound

Product 1

HCID 19040952HCID 19040952, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A stirred solution of 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide (0.5 g, 1.18 mmol) in 10.0 mL of N,N-dimethylformamide is treated with 60% sodium hydride (47 mg, 1.18 mmol) and ethyl bromoacetate (144 μL, 1.3 mmol), and heated at 70° C. for 2.5 hours. The reaction is partitioned between ethyl acetate and water, dried over sodium sulfate and concentrated in vacuo to afford yellow foam. The resulting ethyl 5-[5-(4-cyanophenoxy)pentyloxy]-2-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxyacetate in 50 mL of anhydrous ethanol at 0° C. is treated with anhydrous hydrogen chloride gas over 30 minutes. This solution is stirred at room temperature for 20 hours and concentrated in vacuo. This material is purified by chromatography on silica gel with 60% ethyl acetate/hexane as the eluent to afford ethyl 4-[5-[3-ethoxycarbonylmethoxy-4-[N,N-bis(1- methylethyl)aminocarbonyl]phenoxy]pentyloxy]benzenecarboximidoate monohydrochloride as colorless foam.

Workup

  1. customThe reaction is partitioned between ethyl acetate and water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto afford yellow foam
  5. concentrationconcentrated in vacuo
  6. customThis material is purified by chromatography on silica gel with 60% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-64d84778796846c79f5e43ef4b477f67
Source dataset
uspto-grants-1997_06
Patent number
US05639768

Reaction notes

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