Sodium Hydroxide → HCID 23469722, compound

HRID 128464

Reaction equation

HRID 128464 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[OH-].[Na+].CN([CH:16]=[N:17][C:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)C>O.O1CCOCC1.C(O)(=O)C>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:18]([C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[N:17][CH:16]=[N:10]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 12550338HCID 12550338, compound

Product 1

HCID 23469722HCID 23469722, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A 25.0 g. portion of o-fluorophenylhydrazine hydrochloride is dissolved in 150 ml. of p-dioxane with warming and 31.0 ml. of 5 N sodium hydroxide is added. After solution is complete, 80 ml. of glacial acetic acid and 210 ml. of water are added followed by 28.1 g. of N-(dimethylaminomethylene)-p-nitrobenzamide in 100 ml. of warm p-dioxane. This reaction mixture is heated at 90°-95° C. for 1.5 hours, then cooled and poured into 1500 ml. of water. The solid is collected by filtration, washed with water, dried and crystallized from 200 ml. of ethanol, giving 13.9 g. of the desired product as a tan solid, mp. 143°-145° C.

Workup

  1. temperatureThis reaction mixture is heated at 90°-95° C. for 1.5 hours
  2. temperaturecooled
  3. additionpoured into 1500 ml
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried
  7. customcrystallized from 200 ml
  8. customof ethanol, giving 13.9 g

Sources & evidence

ORD record
ord-769e086f96e04461b8f8105605192835
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Linked notes

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