Chloride → HCID 14281453, compound

HRID 2231223Notes

Reaction equation

HRID 2231223 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([O:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=O)[CH:10]=1.[Cl-].[N:17]1([CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH:21]=[CH:20][N:19]=[CH:18]1>>[N:17]1([CH2:22][CH2:23][CH2:24][CH2:25][N:26]2[C:11](=[O:13])[C:9]3[CH:10]=[CH:1][CH:2]=[C:3]4[C:8]=3[C:7](=[CH:6][CH:5]=[CH:4]4)[C:14]2=[O:15])[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 3

HCID 312ChlorideHCID 6693Naphthalic anhydrideHCID 43794804-(1H-imidazol-1-yl)butan-1-amine

Product 1

HCID 14281453HCID 14281453, compound

Procedure

A mixture of 3.0 g of 1,8-naphthalic anhydride, 50 ml of methyline chloride and 2.1 g of 1H-imidazole-1- butanamine was stirred at room temperature for 20 hours. The insoluble product was isolated by filtration, washed with methlene chloride and then ether and dried in vacuo. The solid was placed in a round-bottom flask and immersed in an oil bath at 150° C., and the temperature was increased over a 45 minute period to 165° C. The reaction mixture was allowed to cool and the residue was triturated with ethyl acetate and recovered by filtration. After recrystallization from ethanol, the desired product melted at 153°-155° C.

Workup

  1. customThe insoluble product was isolated by filtration
  2. washwashed with methlene chloride
  3. dry with materialether and dried in vacuo
  4. customThe solid was placed in a round-bottom flask
  5. customimmersed in an oil bath at 150° C.
  6. temperaturethe temperature was increased over a 45 minute period to 165° C
  7. temperatureto cool
  8. customthe residue was triturated with ethyl acetate
  9. filtrationrecovered by filtration
  10. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-853e68c75af7462db3a00022f3f8bc11
Source dataset
uspto-grants-1988_11
Patent number
US04782064

Reaction notes

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