Diphenyl Ether → HCID 10294261, compound

HRID 1377534Notes

Reaction equation

HRID 1377534 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[O:26]CC=C)=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30]1(OC2C=CC=CC=2)[CH:35]=CC=C[CH:31]=1>>[CH2:35]([C:21]1[C:20]2[O:26][C:16]([CH2:15][C:9]3[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:8]=3)=[N:18][C:19]=2[CH:24]=[C:23]([Cl:25])[CH:22]=1)[CH:30]=[CH2:31]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 15860210HCID 15860210, compound

Product 1

HCID 10294261HCID 10294261, compoundYield 52%

Procedure

A solution of N-(3-cyclopentyloxy-4-methoxyphenylacetyl)-2-allyloxy-5-chloroaniline (38.1 g, 0.092 mol) in 200 ml of diphenyl ether was heated under nitrogen at 180° for 8 hours. Protracted heating resulted in reduced yields. The reaction mixture was diluted with 500 ml of petroleum ether, applied to a column packed with 500 g of flash chromatography silica gel and eluted with petroleum ether followed by methylene chloride. Fractions of 800 ml were collected. The material from fractions 9-14 weighed 30 g (80% of theoretical). This material was recrystallized from hexane to give 19 g (52%) of the title compound, mp 43°-44° C., which was greater than 98.3% pure by HPLC.

Workup

  1. temperatureProtracted heating
  2. customresulted in reduced yields
  3. washeluted with petroleum ether
  4. customFractions of 800 ml were collected
  5. customThis material was recrystallized from hexane

Sources & evidence

ORD record
ord-7303c8a566ed481596f003c23bf6d056
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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