Lithium amide → HCID 13050864, compound

HRID 1648944Notes

Reaction equation

HRID 1648944 reaction equation
CO[C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH3:11])=[CH:5][C:4]=1[C:12]1[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=1.[NH2-:19].[Li+]>O1CCCC1>[NH2:19][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH3:11])=[CH:5][C:4]=1[C:12]1[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=1

Participants

4

Reactant 2

HCID 24532Lithium amideHCID 130508632-(2,3-Dimethoxy-5-methylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Product 1

HCID 13050864HCID 13050864, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In dry tetrahydrofuran (80 ml) was dissolved 2-(2,3-dimethoxy-5-methylphenyl)-4,4-dimethyl-2-oxazoline (5 g). After addition of lithium amide (60 g), the mixture was stirred in a nitrogen gas stream at room temperature for 3 days. To the reaction mixture was added ice-water, followed by extraction with diethyl ether. The solvent layer was washed with water and dried over magnesium sulfate. The solvent was then distilled off to give a brown oil. This oil was chromatographed on silica gel to give colorless prisms (1.2 g) of 2-(2-amino-3-methoxy-5-methylphenyl)-4,4-dimethyl-2-oxazoline.

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe solvent layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. customto give a brown oil
  6. customThis oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-9a2261f7b3ce4a1cbae913f8482ca9d0
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

Loading…