HCID 18368343, compound → HCID 9884882, compound

HRID 379696Notes

Reaction equation

HRID 379696 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:30]=[CH:29][C:15]([NH:16][C:17](=[O:28])[C:18]2[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:19]=2[O:26][CH3:27])=[CH:14][CH:13]=1)=O)(C)(C)C.Cl.O1CCOCC1>>[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:30]=[CH:29][C:15]([NH:16][C:17](=[O:28])[C:18]2[C:19]([O:26][CH3:27])=[CH:20][CH:21]=[CH:22][C:23]=2[O:24][CH3:25])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 18368343HCID 18368343, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 9884882HCID 9884882, compoundYield 83.3%

Procedure

4′-[2-(tert-Butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) was added with 4N HCl/dioxane (5 ml) and mixed for 6 hours at room temperature. The reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (50 ml). The solution was washed with 1N sodium hydroxide aqueous solution (10 ml) followed by saturated sodium chloride (20 ml). After concentration under vacuum to small volume, the solution was subjected to purification by silica-gel column chromatography (chloroform methanol=4:1) to obtain 4′-(2-aminoethoxy)-2,6-dimethoxybenzanilide (0.74 g) as white powder.

Workup

  1. additionmixed for 6 hours at room temperature
  2. concentrationThe reaction mixture was concentrated under vacuum and residue
  3. dissolutionwas dissolved into chloroform (50 ml)
  4. washThe solution was washed with 1N sodium hydroxide aqueous solution (10 ml)
  5. concentrationAfter concentration under vacuum to small volume
  6. customthe solution was subjected to purification by silica-gel column chromatography (chloroform methanol=4:1)

Sources & evidence

ORD record
ord-99ba9c1f3c4f480ea9a3c9bb1a06c07d
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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