tert-Butoxy bis(dimethylamino)methane → HCID 85866839, compound

HRID 751494Notes

Reaction equation

HRID 751494 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][CH:3]=1.C(O[CH:19](N(C)C)[N:20]([CH3:22])[CH3:21])(C)(C)C>>[CH3:19][N:20]([CH3:22])[CH:21]=[CH:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 15480472HCID 15480472, compound

Product 1

HCID 85866839HCID 85866839, compoundYield 107.1%

Procedure

Add 7-methyl-4-nitrobenzofuran (3.5 g, 19.7 mmol) to tert-butoxybis(dimethylamino)methane (10.3 g, 59.1 mmol), and reflux the mixture under nitrogen for 40 minutes. Concentrate under reduced pressure, dissolve in xylenes (50 mL), concentrate under reduced pressure, and dry under vacuum to obtain 4.9 g (100%) of the title compound as a deep red-brown solid. HRMS (M+H)=233.0928.

Workup

  1. temperaturereflux the mixture under nitrogen for 40 minutes
  2. concentrationConcentrate under reduced pressure
  3. dissolutiondissolve in xylenes (50 mL)
  4. concentrationconcentrate under reduced pressure
  5. customdry under vacuum

Sources & evidence

ORD record
ord-537d239adb1f4921a875e477e6249f8a
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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