Triethylamine → 2-(4((6-Chloro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(1,1-difluoro-2,2,2-trichloroethoxy)phenyl)propanamide

HRID 1655543Notes

Reaction equation

HRID 1655543 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[F:25][C:26]([F:39])([O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[C:27]([Cl:30])([Cl:29])[Cl:28].C(N(CC)CC)C.[OH-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:22])[C:19]([NH:36][C:35]3[CH:34]=[CH:33][C:32]([O:31][C:26]([F:25])([F:39])[C:27]([Cl:28])([Cl:29])[Cl:30])=[CH:38][CH:37]=3)=[O:20])=[CH:23][CH:24]=1)[CH:6]=[N:5]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 13370018HCID 13370018, compoundHCID 135292554-(1,1-Difluoro-2,2,2-trichloroethoxy)aniline

Product 1

HCID 197926832-(4((6-Chloro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(1,1-difluoro-2,2,2-trichloroethoxy)phenyl)propanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4.35 mmol of 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)propanoyl chloride (previously prepared from 1.5 g of the corresponding acid) in 15 ml of acetonitrile was added to a mixture prepared from 1.20 g (4.35 mmol) of 4-(1,1-difluoro-2,2,2-trichloroethoxy)aniline, 0.66 g (6.5 mmol) of triethylamine and 10 ml of acetonitrile. The mixture was warmed at reflux for a period of 2.5 hours and then poured over ice and aqueous NaOH added. The resulting precipitate was filtered and dried and then recrystallized from methylcyclohexane. This left 2.2 g (84 percent of theoretical) of the above-named product as a brown solid, m.p. 139°-141° C. (Compound 36)

Workup

  1. additionwas added to a mixture
  2. temperatureThe mixture was warmed
  3. temperatureat reflux for a period of 2.5 hours
  4. additionadded
  5. filtrationThe resulting precipitate was filtered
  6. customdried
  7. customrecrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-cad06a10c03645768c61673b4daa1778
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Reaction notes

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