HCID 20565989, compound → Ammonia
Reaction equation
[NH:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12](N)=[O:13])[CH:8]=[C:7]([NH:15][C:16](N)=[O:17])[CH:6]=1)[C:2](N)=[O:3]>CCOCC>[N:1]([C:5]1[CH:6]=[C:7]([N:15]=[C:16]=[O:17])[CH:8]=[C:9]([N:11]=[C:12]=[O:13])[CH:10]=1)=[C:2]=[O:3].[NH3:1]Participants
Reactant 1
Product 2
Reagents, catalysts & solvents 1
Procedure
Like the triamide, 1,3,5-triureido benzene is also known. It is obtained from 1,3,5-triisocyanato-benzene with ammonia in ether (Gill et al., Soc. 1949, 1753; WG P 815 486). With the process according to the invention it is formed by treatment of benzene tricarboxylic acid-(1,3,5)-tri-N-chloramide with ammonia. Expediently, tri-N-chloramide is suspended in water, reacted with ammonia in the presence of cooling, followed by vigorous mixing of the reaction mixture. The reaction mixture should thereby never exceed a temperature of 25° C. Once the sediment is fully dissolved, the solution is quickly heated to the boil and kept at this temperature for about 15 to 30 min. After cooling, the precipitated 1,3,5-triureido-benzene is filtered off, washed and dried. At least stoichiometric quantities of ammonia are used hereby, i.e. one mole benzene tricarboxylic acid-(1,3,5)-tri-N-chloramide requires 6 moles of ammonia. It is advantageous to use up to 10 mole % excess ammonia and after separation of 1,3,5-triureido-benzene to use the filtrate for the reaction of additional tri-N-chloramide. The yield in this process step exceeds 97% of the theory.
Sources & evidence
- ORD record
- ord-94adf14eef8142cbb498b957e9bf33e7
- Source dataset
- uspto-grants-1978_10
- Patent number
- US04123461
Reaction notes
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