Water → HCID 57567342, compound

HRID 2404740Notes

Reaction equation

HRID 2404740 reaction equation
C([O-])(O)=O.[Na+].[CH3:6][O:7][CH2:8][CH2:9][O:10][CH2:11][C:12]([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])([CH3:14])[CH3:13].[C:25](Cl)(=[O:27])[CH3:26].O>ClCCl>[CH3:6][O:7][CH2:8][CH2:9][O:10][CH2:11][C:12]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:25](=[O:27])[CH3:26])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 575673834-[2-(2-Methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenylamine

Product 1

HCID 57567342HCID 57567342, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a suspension of NaHCO3 (10 g, 0.1 mol) in dichloromethane (50 mL) was added 4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenylamine (5 g, 30 mmol) and acetyl chloride (3 mL, 20 mmol) at 0-5° C. The mixture was stirred overnight at 15° C. and then poured into water (200 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL×2). The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated to dryness to give N-{4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenyl}-acetamide (5.0 g, 87%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (50 mL×2)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2aa868a7d81e47aead4a9eef1569ef20
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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