Isatoic Anhydride → HCID 13952771, compound
Reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:5]=[CH:4][N:3]=[CH:2]1.[C:12]12[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH:17][C:16](=O)[O:15][C:13]2=[O:14]>C(O)C>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:13](=[O:14])[C:12]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 1.53 g of 1H-imidazole-1-pentanamine, 1.63 g of isatoic anhydride and 15 ml at ethanol was stirred for 20 hours and concentrated. The viscous residue was mixed with 10 ml of ethyl chloroformate and heated for 1.5 hours in an oil bath at 95° C. The mixture was dissolved in ethanol, reconcentrated, mixed with 2.0 g of potassium hydroxide and 50 ml of ethanol and heated at reflux temperature for 3 hours. The reaction mixture was concentrated, dissolved in water and treated with acetic acid to pH 6-7. The insoluble material was collected by filtration and recrystallized from ethanol to obtain the desired product, mp 160°-162° C.
Workup
- concentrationconcentrated
- additionThe viscous residue was mixed with 10 ml of ethyl chloroformate
- dissolutionThe mixture was dissolved in ethanol
- additionmixed with 2.0 g of potassium hydroxide and 50 ml of ethanol
- temperatureheated
- temperatureat reflux temperature for 3 hours
- concentrationThe reaction mixture was concentrated
- dissolutiondissolved in water
- additiontreated with acetic acid to pH 6-7
- filtrationThe insoluble material was collected by filtration
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-72ca5329042648c3adc923f1baeaf804
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04684654
Reaction notes
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