tert-Butoxy bis(dimethylamino)methane → beta-Dimethylamino4-methoxy-2,3-dinitrostyrene

HRID 1032533Notes

Reaction equation

HRID 1032533 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([N+:10]([O-:12])=[O:11])[C:4]=1[N+:13]([O-:15])=[O:14].[CH3:16][N:17]([CH:19](N(C)C)OC(C)(C)C)[CH3:18]>>[CH3:16][N:17]([CH3:19])[CH:18]=[CH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]=1[N+:10]([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 122382934-Methoxy-2,3-dinitrotoluene

Product 1

HCID 54312252beta-Dimethylamino4-methoxy-2,3-dinitrostyrene

Procedure

57.7 g of 4-methoxy-2,3-dinitrotoluene (J. Chem. Soc. 1927:580) is agitated with 150 ml of bisdimethylamino-tert-butoxymethane [Chem. Ber. 101:41 (1968)] for 6 hours at 80° C. After cooling, the precipitated solid material is filtered off, washed with diisopropyl ether, and dried with a water-jet aspirator, thus producing 54.6 g of β-dimethylamino4-methoxy-2,3-dinitrostyrene, mp 100°-131° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid material is filtered off
  3. washwashed with diisopropyl ether
  4. dry with materialdried with a water-jet aspirator

Sources & evidence

ORD record
ord-88309c5d36d640aa8471e4572dcbab7e
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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