Sodium Hydroxide → 5-Hexadecylamino-2-furancarboxylic acid

HRID 850972Notes

Reaction equation

HRID 850972 reaction equation
[CH2:1]([NH:17][C:18]1[O:22][C:21]([C:23]([O:25]CC)=[O:24])=[CH:20][CH:19]=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].[OH-].[Na+]>C(O)C>[CH2:1]([NH:17][C:18]1[O:22][C:21]([C:23]([OH:25])=[O:24])=[CH:20][CH:19]=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 2

HCID 14798Sodium HydroxideHCID 20503623Ethyl 5-hexadecylamino-2-furancarboxylate

Product 1

HCID 205036575-Hexadecylamino-2-furancarboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.0 g. of ethyl 5-hexadecylamino-2-furancarboxylate, 10 ml. of ethanol, and 2.0 ml. of 1 N sodium hydroxide is stirred under reflux for 3 hours and then allowed to cool. The mixture is concentrated in vacuo, diluted with water, and adjusted to pH 5 with the dropwise addition of dilute hydrochloric acid. The solid is collected by filtration, washed with water, and dried to yield the product.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. concentrationThe mixture is concentrated in vacuo
  5. additiondiluted with water
  6. additionadjusted to pH 5 with the dropwise addition of dilute hydrochloric acid
  7. filtrationThe solid is collected by filtration
  8. washwashed with water
  9. customdried
  10. customto yield the product

Sources & evidence

ORD record
ord-d85e19d7ea044d4c8ed8d6e2576d653b
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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