Water → HCID 69020977, compound

HRID 2091975Notes

Reaction equation

HRID 2091975 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][OH:6])[CH3:2].[H-].[Na+].[Br:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1N.O.C(Cl)(Cl)[Cl:24]>CC(N(C)C)=O>[ClH:24].[Br:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[O:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2]

Participants

7

Reactant 5

HCID 962WaterHCID 6212ChloroformHCID 7497DiethylethanolamineHCID 24758Sodium hydrideHCID 25840Benzenamine, 2-bromo-4-nitro-

Product 1

HCID 69020977HCID 69020977, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-(diethylamino)ethanol (0.59 g, 5 mmol) in DMA (5 ml), sodium hydride (0.24 g, 10 mmol) was added in one portion. Fifteen minute later 2-bromo-4-nitroaniline (1.1 g, 5 mmol) was added and the content was stirred for 4 hr. Water (50 ml) was added to the reaction mixture followed by chloroform. The organic layer was separated, washed with saturated sodium bicarbonate follow by brine. The organic layer was dried over sodium sulfate and concentrated to oil. The oil was dissolved in methanol and saturated with HCl gas. The resulting solution was concentrated and diethyl ester was added. The resulting precipitate was washed with ether and dried to yield 0.8 g of 2-[(2-bromo-4-nitrophenyl)Oxy]-N,N-diethylethanamine hydrochloride as a solid. LCMS: m/z 318 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated to oil
  5. dissolutionThe oil was dissolved in methanol and saturated with HCl gas
  6. concentrationThe resulting solution was concentrated
  7. additiondiethyl ester was added
  8. washThe resulting precipitate was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-938b9541f99a4c1b8baf970ca0cf6875
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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