Water → HCID 1234606, compound

HRID 1639217Notes

Reaction equation

HRID 1639217 reaction equation
[C:1]1([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]([NH2:7])=[CH:5][CH:6]=1.N1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16](Cl)(=[O:25])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH2:27]>O1CCOCC1>[C:11]([NH:8][C:2]1[C:1]([CH3:9])=[CH:6][CH:5]=[C:4]([NH:7][C:16](=[O:25])[CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1)(=[O:27])[CH:12]=[CH:13][C:14]1[CH:15]=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 72612,4-DiaminotolueneHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 1234606HCID 1234606, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
25 °C

Procedure

In a 1 liter, 4 neck, flask equipped with a mechanical stirrer, thermometer, water condenser, and dropping funnel was placed 36.9 grams (0.3 moles) 2,4-toluenediamine, 48 grams pyridine, and 150 milliliters 1,4-dioxane. The flask and its contents were then cooled to 25° C. by means of an ice-water bath. To this cooled and stirred mixture was added by means of the dropping funnel a solution of 100 grams (0.6 moles) cinnamoyl chloride in 100 milliliters 1,4-dioxane. The addition required 0.5 hr. during which time the temperature of the flask and its contents was maintained between 25°-30° C. Upon completion of the addition the contents of the flask were allowed to stir at 25°-30° C. for an additional 0.5 hr. then poured into 500 milliliters of cold water which immediately caused the precipitation of light amber color solids. The solids were collected by suction filtration, partially dried, and recrystallized from 1,4-dioxane giving 98.0 grams (85.5% ) of light lemon color crystals. Recrystallization of this material from ethyl alcohol containing powdered charcoal gave 74 grams (64.6% yield) of pure white crystals which melted at 217°-219° C.

Workup

  1. customIn a 1 liter, 4 neck, flask equipped with a mechanical stirrer
  2. customthermometer, water condenser, and dropping
  3. customfunnel was placed
  4. temperatureTo this cooled
  5. additionThe addition required 0.5 hr
  6. temperatureduring which time the temperature of the flask and its contents was maintained between 25°-30° C
  7. additionUpon completion of the addition the contents of the flask
  8. stirringto stir at 25°-30° C. for an additional 0.5 hr
  9. customthe precipitation of light amber color solids
  10. filtrationThe solids were collected by suction filtration
  11. custompartially dried
  12. customrecrystallized from 1,4-dioxane giving 98.0 grams (85.5% ) of light lemon color crystals
  13. customRecrystallization of this material from ethyl alcohol containing powdered charcoal

Sources & evidence

ORD record
ord-0f20ab6821b94bdeaf364bc0973584c2
Source dataset
uspto-grants-1989_11
Patent number
US04883653

Reaction notes

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