Nitrogen → HCID 13656082, compound

HRID 2232170Notes

Reaction equation

HRID 2232170 reaction equation
N#N.[H-].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[CH:10][C:11]=1[Cl:12].[C:14]([NH:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][CH2:24][CH2:25]Cl)=[CH:20][CH:19]=1)(=[O:16])[CH3:15]>CN(C=O)C>[C:14]([NH:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][CH2:24][CH2:25][O:13][C:8]2[CH:9]=[CH:10][C:11]([Cl:12])=[C:6]([Cl:5])[CH:7]=2)=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 947NitrogenHCID 72583,4-DichlorophenolHCID 24758Sodium hydrideHCID 5147668N-[4-(3-chloropropoxy)phenyl]acetamide2×

Product 1

HCID 13656082HCID 13656082, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a round bottomed flask equipped with magnetic stirring, reflux condenser, N2 atmosphere, and a heating mantle was placed DMF (80 ml) and to this was added cautiously NaH (60% by weight in oil, 1.76 g) followed by 3,4-dichlorophenol (7.15 g). This mixture was stirred for ten minutes then 1-[4-acetamidophenoxy]-3-chloropropane of Formula XXI (10.0 g) was added; and the reaction mixture heated at 80° C. overnight. The mixture was cooled and the DMF removed in vacuo. The residue was poured into ice water and the precipitated brown solid was collected by filtration. The crude product was recrystallized from ethanol to give an off white solid (9.8 g), mp 135°-7° C.

Workup

  1. customIn a round bottomed flask equipped with magnetic stirring
  2. temperaturereflux condenser
  3. temperatureThe mixture was cooled
  4. customthe DMF removed in vacuo
  5. additionThe residue was poured into ice water
  6. filtrationthe precipitated brown solid was collected by filtration
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-61260405aa8442569375b5aea573d897
Source dataset
uspto-grants-1988_11
Patent number
US04786755

Reaction notes

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