tert-Butoxy bis(dimethylamino)methane → 1-(3-Benzyloxy-4-nitrophenyl)-2-dimethylaminoethene

HRID 1032518Notes

Reaction equation

HRID 1032518 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:18])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:24](N(C)C)[N:25]([CH3:27])[CH3:26])(C)(C)C>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:24][N:25]([CH3:27])[CH3:26])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 136293042-(Benzyloxy)-4-methyl-1-nitrobenzene

Product 1

HCID 540490861-(3-Benzyloxy-4-nitrophenyl)-2-dimethylaminoetheneYield 95.3%

Procedure

16.0 g of 3-benzyloxy-4-nitrotoluene and 23.0 g of tert-butoxybis(dimethylamino)methane are heated for 8 hours to 100° C. After allowing the mixture to stand for 8 hours at room temperature, the pure reaction product is crystallized. This product is filtered off and washed with a mixture of ethyl acetate and cyclohexane 1:4, thus obtaining 18.7 g of 1-(3-benzyloxy-4-nitrophenyl)-2-dimethylaminoethene, mp 111°-114° C.

Workup

  1. customthe pure reaction product is crystallized
  2. filtrationThis product is filtered off
  3. washwashed with a mixture of ethyl acetate and cyclohexane 1:4

Sources & evidence

ORD record
ord-ae2245a3cfd8447ea4807d5843602a22
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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