Sulfuric Acid → HCID 12674764, compound

HRID 67109Notes

Reaction equation

HRID 67109 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1.S(=O)(=O)(O)O.N1C=CC=C1.[C:19](Cl)(=[O:21])[CH3:20].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:19]([O:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)(=[O:21])[CH3:20]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6367Acetyl chloride2×HCID 7918Acetic Anhydride2×HCID 8027PyrroleHCID 109754381-(2-Hydroxyethyl)pyrrole2×

Product 1

HCID 12674764HCID 12674764, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Once the 1-(2-hydroxyethyl)pyrrole is obtained, it is esterified by any suitable means known in the art. Suitably, acetic acid is reacted with the 1-(2-hydroxyethyl)pyrrole in the presence of a strong acid such as sulfuric acid and heating the reaction mixture sufficiently to distill off the water that is formed as a result of the reaction. Preferably however, the pyrrole is reacted with acetyl chloride or acetic anhydride in a suitable solvent wherein there is a molar excess of the acetyl chloride or acetic anhydride. The reaction takes place at room temperature and will be completed in a relatively short period of time, with only an hour or two at the most being required for the reaction to reach completion. The 1-(2-acetoxyethyl)pyrrole is then isolated and purified by any means known in the art such as extraction with a suitable organic solvent and removal of the solvent to yield the desired compound represented by Formula (III).

Workup

  1. temperatureheating the reaction mixture sufficiently
  2. distillationto distill off the water that
  3. customis formed as
  4. customa result of the reaction
  5. customat room temperature
  6. waitwill be completed in a relatively short period of time, with only an hour
  7. customtwo at the most being required for the reaction

Sources & evidence

ORD record
ord-f770c4c3d4424493bd96bf077e2c6ba2
Source dataset
uspto-grants-1982_08
Patent number
US04344943

Reaction notes

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