Epichlorohydrin → 2-[(4-Methyl-2,3-dinitrophenoxy)methyl]oxirane
Reaction equation
[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([CH3:13])[CH:7]=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].Cl[CH2:16][CH:17]1[O:19][CH2:18]1.[OH-].[Na+]>>[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([CH3:13])[CH:7]=[CH:6][C:5]=1[O:14][CH2:16][CH:17]1[O:19][CH2:18]1)([O-:3])=[O:2]Participants
4
Procedure
2,3-Dinitro-4-methylphenol (see H. E. Dadswell and J. Kenner, J. Chem. Soc., 1927, 583) is reacted with 3-chloro-1,2-epoxypropane and 25% aqueous sodium hydroxide solution to give, in a yield of 78% of theory, 2,3-dinitro-1-(2,3-epoxypropoxy)-4-methylbenzene (m.p. 121°-123° C.). This compound is reacted in boiling ethanol with tert.-butylamine to give 2,3-dinitro-1-(2-hydroxy-3-tert.-butylaminopropoxy, 4-methylbenzene (m.p. 104°-106° C.), catalytic hydrogenation of which, in the presence of platinum dioxide, gives amorphous 2,3-diamino-1-(2-hydroxy-3-tert.-butylaminopropoxy)-4-methylbenzene trihydrochloride.
Sources & evidence
- ORD record
- ord-62ac0f88534e487098286d3d99f0b761
- Source dataset
- uspto-grants-1983_01
- Patent number
- US04367235
Reaction notes
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