Chloroform → (-)-N-[1-(Methoxymethyl)propyl]-2,6-dinitro-3,4-xylidine
Reaction equation
[C:1]([OH:5])(C)(C)C.[CH2:6]([NH2:9])[CH2:7][CH3:8].Cl[C:11]1[C:12]([N+:22]([O-:24])=[O:23])=[C:13]([CH3:21])[C:14]([CH3:20])=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18].[CH:25](Cl)(Cl)Cl>>[CH3:25][O:5][CH2:1][CH:6]([NH:9][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([CH3:20])=[C:13]([CH3:21])[C:12]=1[N+:22]([O-:24])=[O:23])[CH2:7][CH3:8]Participants
Procedure
(-)-2-Amino-1-butanol [100 grams, prepared according to D. Pitre and E. B. Grabitz, Chimia 23, 399 (1969)] was added in a dropwise manner to a stirred solution of tert-butanol (800 ml.) containing potassium tert-butoxide (126 grams). After warming this mixture to 70° C. to 80° C. for 2 hours, methyl iodide (175 grams) was added slowly at temperatures below 50° C. The suspension which formed was then stirred with refluxing overnight. After removal of the solid phase by filtration, the filtrate was fractionally distilled to give (-)-1-methoxymethyl)propylamine contaminated with traces of tert-butanol, boiling point 125° C. to 147° C./760 mm. This amine was then allowed to react with 4-chloro-3,5-dinitro-o-xylene, as described earlier, to give the desired product as a bright yellow solid with melting point 42.5° C. to 44° C., [α]D25° =-137.6° (c 2.504, chloroform).
Sources & evidence
- ORD record
- ord-0882ecccbd94414a850ec8bbb6cb3ec6
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04025538
Reaction notes
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