Hydrochloric Acid → N,N-dimethyl-N-(4-nitrophenyl)carbamylmethyl-N-3-aminopropylammonium chloride
Reaction equation
[Cl-:1].[CH3:2][N+:3]([CH3:23])([CH2:10][C:11](=[O:22])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH2:6][NH:7]C=O.Cl.[OH-].[Na+]>O>[Cl-:1].[CH3:23][N+:3]([CH3:2])([CH2:10][C:11](=[O:22])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH2:6][NH2:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 10.0 parts of N,N-dimethyl-N-(4-nitrophenyl)carbamylmethyl-N-3-formamidopropylammonium chloride in 100 parts of water containing 6.0 parts of concentrated hydrochloric acid was heated for about two hours. The reaction mixture was rendered slightly alkaline by the addition of 50 percent aqueous sodium hydroxide and stored in the refrigerator for 2 days. The reaction mixture was then filtered to remove a small amount of solid and the filtrate was acidified with 48 parts of concentrated hydrochloric acid. Acetone was slowly added to the acidified filtrate until precipitation started. When precipitation of the product was complete, the solid was collected on a filter, washed with acetone, and dried at 75° C. to obtain 8.2 parts of N,N-dimethyl-N-(4-nitrophenyl)carbamylmethyl-N-3-aminopropylammonium chloride as the mono-hydrochloride salt, a white solid which melted at 244°-245° C.
Workup
- filtrationThe reaction mixture was then filtered
- customto remove a small amount of solid
- additionAcetone was slowly added to the acidified filtrate until precipitation
- customWhen precipitation of the product
- customthe solid was collected on a filter
- washwashed with acetone
- customdried at 75° C.
Sources & evidence
- ORD record
- ord-88073dd9643d46da9a38ba0e31b4a63c
- Source dataset
- uspto-grants-1978_07
- Patent number
- US04103092
Reaction notes
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