HCID 13746074, compound → HCID 13746076, compound

HRID 2290922Notes

Reaction equation

HRID 2290922 reaction equation
[CH3:1][O:2][C:3]1[C:10]2[CH:9]=[C:8]([C:11]([NH:13][CH2:14][CH:15]=[CH2:16])=[O:12])[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH3:18]>ClC1C=CC=CC=1Cl>[CH3:1][O:2][C:3]1[C:10]2[CH2:9][CH2:16][C@H:15]3[C@@H:8]([C:11](=[O:12])[NH:13][CH2:14]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH3:18]

Participants

3

Reactant 1

HCID 13746074HCID 13746074, compound

Product 1

HCID 13746076HCID 13746076, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 3,4-dimethoxy-N-(2-propenyl)benzocyclobutene-1-carboxamide (13.2 g, 0.053 mole) and o-dichlorobenzene (600 mL) was stirred at reflux for 15 hours. After cooling to 0°, a solid was filtered, washed with hexane, and dried (in-vacuo) to yield 6.8 g white solid. cis And trans isomers were separated by HPLC to obtain: 1.80 g trans isomer; mp 185°-7°; M+ 247; and 3.50 g cis isomer; mp 219°-21°; M+ 247.

Workup

  1. temperatureat reflux for 15 hours
  2. temperatureAfter cooling to 0°
  3. filtrationa solid was filtered
  4. washwashed with hexane
  5. customdried (in-vacuo)

Sources & evidence

ORD record
ord-d49bac2421d546aa8e74365358867582
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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