Isopropylamine → HCID 53740103, compound

HRID 379717Notes

Reaction equation

HRID 379717 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=2[CH3:24])(=O)=O)=CC=1.[CH:26]([NH2:29])([CH3:28])[CH3:27]>O1CCOCC1>[CH:26]([NH:29][CH2:11][CH2:12][O:13][C:14]1[C:15]([CH3:24])=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[CH:18][C:19]=1[CH3:20])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 18368336HCID 18368336, compound

Product 1

HCID 53740103HCID 53740103, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-(2,6-Dimethyl-4-nitrophenoxy)ethyl p-toluenesulfonate (10.0 g) solution in dioxane (15 ml) was added with isopropylamine (10 ml) and the mixture was stirred for 3 hours in an autoclave at 80° C. After being concentrated , the reaction mixture was dissolved into ethyl acetate (50 ml) and extracted with 1N HCl (150 ml). Resultant aqueous layer was added with 1N sodium hydroxide (200 ml) and extracted with chloroform (200 ml). After being dehydrated with anhydrous magnesium sulfate (20 g), chloroform layer was concentrated under vacuum to dryness to obtain N-isopropyl-[2-(2,6-dimethyl-4-nitrophenoxy)]ethylamine (5.5 g) as yellowish solid.

Workup

  1. concentrationAfter being concentrated
  2. dissolutionthe reaction mixture was dissolved into ethyl acetate (50 ml)
  3. extractionextracted with 1N HCl (150 ml)
  4. additionResultant aqueous layer was added with 1N sodium hydroxide (200 ml)
  5. extractionextracted with chloroform (200 ml)
  6. concentrationwas concentrated under vacuum to dryness

Sources & evidence

ORD record
ord-27ff71787c3a46dda3a243a740abb49a
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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