Hydrochloric Acid → HCID 19040952, compound

HRID 2399953Notes

Reaction equation

HRID 2399953 reaction equation
[OH:1][C:2]1C=CC=C[C:3]=1C(N(C(C)C)C(C)C)=O.[H-].[Na+].BrCC(OCC)=O.[C:26]([C:28]1[CH:62]=[CH:61][C:31]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39]2[CH:40]=[CH:41][C:42]([C:52]([N:54]([CH:58]([CH3:60])[CH3:59])[CH:55]([CH3:57])[CH3:56])=[O:53])=[C:43]([CH:51]=2)[O:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:30][CH:29]=1)#[N:27].[ClH:63]>CN(C)C=O.C(O)C>[ClH:63].[CH2:49]([O:48][C:46]([CH2:45][O:44][C:43]1[CH:51]=[C:39]([CH:40]=[CH:41][C:42]=1[C:52]([N:54]([CH:58]([CH3:60])[CH3:59])[CH:55]([CH3:56])[CH3:57])=[O:53])[O:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][O:32][C:31]1[CH:30]=[CH:29][C:28]([C:26](=[NH:27])[O:1][CH2:2][CH3:3])=[CH:62][CH:61]=1)=[O:47])[CH3:50]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 2253642-Hydroxy-N,N-di(propan-2-yl)benzamideHCID 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 4-15-(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-b01c2aa6bb3c4edc949d9d91bac79253
Source dataset
uspto-grants-1995_09
Patent number
US05451700

Reaction notes

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