Ethanol → HCID 54281164, compound

HRID 2051788Notes

Reaction equation

HRID 2051788 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH3:20])=[C:15]([CH:19]=2)[C:16]([OH:18])=[O:17])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:28](O)[CH3:29]>>[CH2:28]([O:17][C:16](=[O:18])[C:15]1[CH:19]=[C:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:22][CH:21]=2)[CH:12]=[CH:13][C:14]=1[CH3:20])[CH3:29]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 20378358HCID 20378358, compound

Product 1

HCID 54281164HCID 54281164, compound

Procedure

6 Grams of 5-(2-[4-chloro-benzamido]-ethyl)-2-methyl-benzoic acid in 50 ml of ethanol are boiled for 4 hours with 1.5 ml of concentrated sulfuric acid at the reflux condenser. Subsequently the alcohol is distilled off for the most part, the residue is mixed with ice, the precipitate is filtered off with suction, is treated with diluted ammonia in order to remove the acid still present and is recrystallized from diluted ethanol. The 5-(2-[4-chloro-benzamido]-ethyl)-2-methyl-benzoic acid-ethylester obtained melts at a temperature in the range of from 116° to 118° C.

Workup

  1. distillationSubsequently the alcohol is distilled off for the most part
  2. additionthe residue is mixed with ice
  3. filtrationthe precipitate is filtered off with suction
  4. additionis treated with diluted ammonia in order
  5. customto remove the acid still present
  6. customis recrystallized from diluted ethanol
  7. customof from 116° to 118° C.

Sources & evidence

ORD record
ord-285c97a14ab848eeaa1805e931aaad73
Source dataset
uspto-grants-1980_01
Patent number
US04182775

Reaction notes

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