Hydrochloric Acid → HCID 53905596, compound

HRID 485247Notes

Reaction equation

HRID 485247 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[CH:7][C:8]([NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[CH:7][C:8]([NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium Hydroxide2×HCID 692488p-(p-Chlorocinnamamido)benzoic acid, ethyl ester

Product 1

HCID 53905596HCID 53905596, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 7.1 g. of p-(p-chlorocinnamamido)benzoic acid, ethyl ester and 1.6 g. of potassium hydroxide in 50 ml. of 95% ethanol is stirred at 75° C. overnight. A 25 ml. portion of water and 200 mg. of potassium hydroxide are added, and stirring is continued at 75° C. for 1.5 hours. The mixture is then diluted with 150 ml. of water, adjusted to pH 3 with 37% hydrochloric acid, and the precipitate is collected and dried. The solid is boiled in 100 ml. of methyl cellosolve, cooled, and the solid is collected, washed with ethanol, and dried, giving 5.51 g. of the desired product as a white powder, m.p. 333°-336° C. (dec.).

Workup

  1. additionThe mixture is then diluted with 150 ml
  2. customthe precipitate is collected
  3. customdried
  4. temperatureof methyl cellosolve, cooled
  5. customthe solid is collected
  6. washwashed with ethanol
  7. customdried
  8. customgiving 5.51 g

Sources & evidence

ORD record
ord-920d51f5348e4060b245c5a042c489c8
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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