Furfurylamine → 2-chloro-N-(2-furylmethyl)acetamide

HRID 256467Notes

Reaction equation

HRID 256467 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:10][CH2:11][C:12](Cl)=[O:13]>C1(C)C=CC=CC=1>[CH2:1]([NH:7][C:12](=[O:13])[CH2:11][Cl:10])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3438FurfurylamineHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 7209222-chloro-N-(2-furylmethyl)acetamideYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Furfurylchloroacetamide was prepared by adding 20.0 g. (0.206 mole) furfuryl amine in sufficient toluene to make a 15% solution to a 500 ml. three neck round bottom flask equipped with magnetic stir bar, additional funnel, and cooling bath and then adding 36 ml. of 20% sodium hydroxide. The mixture was cooled to 0°-5° C. and chloroacetyl chloride was added dropwise so that the reaction temperature was maintained at 5°-10° C. After the addition, a solid deposited on the walls of the flask. It was recrystallized from ether as a light tan solid. Yield was 85%.

Workup

  1. additionby adding 20.0 g
  2. customthree neck round bottom flask equipped with magnetic stir bar, additional funnel
  3. temperaturecooling bath
  4. additionadding 36 ml
  5. temperatureThe mixture was cooled to 0°-5° C.
  6. temperaturewas maintained at 5°-10° C
  7. additionAfter the addition
  8. customIt was recrystallized from ether as a light tan solid

Sources & evidence

ORD record
ord-dfd57f5b61284c5bb698f76d5a2e50f4
Source dataset
uspto-grants-1987_10
Patent number
US04703116

Reaction notes

Loading…