Toluene → HCID 13175523, compound

HRID 434476Notes

Reaction equation

HRID 434476 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](Cl)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([NH:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1)[CH3:19].C1(C)C=CC=CC=1>C(O)C>[CH2:18]([N:20]([CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1)[C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 751764-tert-Butyl-2,6-dinitrochlorobenzeneHCID 13175522HCID 13175522, compound

Product 1

HCID 13175523HCID 13175523, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

4-t-butyl-2,6-dinitro chlorobenzene (2.5 grams; 0.01 mole), 2-(ethylamino)methyl-2-methyl-1,3-dioxolane (2.9 grams; 0.02 mole) and toluene (50 ml) were placed into a glass reaction vessel equipped with a stirrer, oil bath and thermometer and heated to 70° C. with stirrer for 30 hours. Ethanol (50 ml) was added to the cooled mixture and the solid filtered therefrom. The filtrate was evaporated to a volume of approximately 10 ml. It was then chromatographed on silica gel to yield the desired product (2.0 grams). The product was analyzed for C17H25N3O6 :

Workup

  1. customequipped with a stirrer, oil bath
  2. filtrationthe solid filtered
  3. customThe filtrate was evaporated to a volume of approximately 10 ml
  4. customIt was then chromatographed on silica gel

Sources & evidence

ORD record
ord-de022729a46d4e76a3efe7d22a9b1556
Source dataset
uspto-grants-1983_08
Patent number
US04397677

Reaction notes

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