Ammonia → 2-[4-[(2-amino-5-butoxy-4-iminocyclohexa-2,5-dien-1-ylidene)amino]-N-(2-hydroxyethyl)anilino]ethanol
Reaction equation
Cl.[CH2:2]([N:4](C(C)C)[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:3].Cl.Cl.[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][C:23]=1[NH2:29])[CH2:18][CH2:19][CH3:20].N.[OH:31]O.[CH2:33]([OH:35])[CH3:34]>O>[NH2:28][C:25]1[C:26](=[N:11][C:8]2[CH:9]=[CH:10][C:5]([N:4]([CH2:2][CH2:3][OH:31])[CH2:34][CH2:33][OH:35])=[CH:6][CH:7]=2)[CH:27]=[C:22]([O:21][CH2:17][CH2:18][CH2:19][CH3:20])[C:23](=[NH:29])[CH:24]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 0.925 g (0.003 mol) of N-ethyl-N-isopropyl-4-aminoaniline hydrochloride and 0.76 g (0.003 mol) of 4-butoxybenzene-1,3-diamine dihydrochloride in 2 ml of water and 6 ml of ethanol, brought to pH 9.5 with 20% aqueous ammonia, are added 10.2 ml of 6% aqueous hydrogen peroxide solution. After stirring for 24 hours at room temperature, the ethanol is removed and the coupling product formed is extracted with butanol. After removal of the butanol under vacuum, the gummy residue is taken up in ethyl acetate and then in ether. 0.470 g of 2-[[4-(2-amino-5-butoxy-4-iminocyclohexa-2,5-dienylideneamino)phenyl](2-hydroxyethyl)amino]ethanol 10 is obtained in the form of a blue-black powder after drying.
Workup
- customthe ethanol is removed
- customthe coupling product formed
- extractionis extracted with butanol
- customAfter removal of the butanol under vacuum
Sources & evidence
- ORD record
- ord-00d1f0ebe0fa4bef90831e3d948b2145
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226883B2
Reaction notes
Loading…