Sulfuric Acid → HCID 20503613, compound

HRID 850975Notes

Reaction equation

HRID 850975 reaction equation
[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:24]([O:26]CC)=[O:25])[N:21]([CH3:23])[CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>>[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:24]([OH:26])=[O:25])[N:21]([CH3:23])[CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 20503645HCID 20503645, compound

Product 1

HCID 20503613HCID 20503613, compound

Procedure

A mixture of 1.0 g. of ethyl 4-hexadecylamino-1-methyl-2-pyrrolecarboxylate and 10 ml. of 40% aqueous sulfuric acid is heated under reflux for 24 hours, allowed to cool and neutralized with sodium acetate. The mixture is extracted with chloroform and the extract is dried over magnesium sulfate and evaporated. The residue is purified by chromatography on a silica gel column by elution with chloroform-acetic acid mixtures. Evaporation of the eluate affords the product.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureunder reflux for 24 hours
  3. temperatureto cool
  4. extractionThe mixture is extracted with chloroform
  5. dry with materialthe extract is dried over magnesium sulfate
  6. customevaporated
  7. customThe residue is purified by chromatography on a silica gel column by elution with chloroform-acetic acid mixtures
  8. customEvaporation of the
  9. customeluate affords the product

Sources & evidence

ORD record
ord-895c993249f4446ba201538680ddbaa2
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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