N,N-Diethylaniline → HCID 19093016, compound

HRID 487731Notes

Reaction equation

HRID 487731 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[N+:15]([O-:17])=[O:16].C(N(CC)C1C=CC=CC=1)C.Cl[CH2:30][O:31][CH3:32]>C(Cl)(Cl)Cl>[CH3:30][O:31][CH2:32][O:1][CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7864Chloromethyl Methyl EtherHCID 19093003HCID 19093003, compound

Product 1

HCID 19093016HCID 19093016, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2-hydroxymethyl-1-nitro-3,4,5-trimethoxybenzene (6.5 g, 26.7 mmol) and N,N-diethylaniline (9.96 g, 66.8 mmol) in dry chloroform (150 ml) was added dropwise chloromethylmethyl ether (4.28 g, 53.5 mmol) in an ice-bath. After stirring at room temperature overnight, the reaction mixture was washed successively with 1% hydrochloric acid, water, 10% sodium bicarbonate solution and water, and dried over sodium sulfate. The solvent was removed by evaporation in vacuo and the residue was crystallized from hexane to give 7.62 g (99%) of 2-methoxymethoxymethyl-1-nitro-3,4,5-trimethoxybenzene, mp. 39-40 ° C. 1H-NMR (CDCl3): δ3.40 (3H, s, CH2OMe), 3.93 (6H, s, 2×OMe), 3.94 (3H, s, 1×OMe), 4.73 and 4.82 (each 2H, s, 2 ×CH2), 7.29 (1H, s, H-6). Analyses: Calculated for C12H17NO7 : C, 50.17; H, 5.59; N, 4.88. Found: C, 50.18; H, 5.92; N, 4.80.

Workup

  1. washthe reaction mixture was washed successively with 1% hydrochloric acid, water, 10% sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed by evaporation in vacuo
  4. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-39af6147796846df89ecce8770175df8
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

Loading…