1,2-Dimethoxyethane → 2-[2-(4-Tetradecenylamino)phenyl]oxazoline

HRID 325574

Reaction equation

HRID 325574 reaction equation
Br.Br[CH2:3][CH2:4][NH2:5].COCCOC.Cl.[CH2:13]([NH:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31])[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH2:13]([NH:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]1[O:31][CH2:3][CH2:4][N:5]=1)[CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 80711,2-Dimethoxyethane2×HCID 27742172-Bromoethylamine hydrobromideHCID 737080852-(4-Tetradecenylamino)benzoyl chloride hydrochloride

Product 1

HCID 540061592-[2-(4-Tetradecenylamino)phenyl]oxazoline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To a slurry of 15 g. of 2-bromoethylamine hydrobromide in 150 ml. of 1,2-dimethoxyethane are added simultaneously solutions of 31 g. of 2-(4-tetradecenylamino)benzoyl chloride hydrochloride in 60 ml. of 1,2-dimethoxyethane and 50 cc. of triethylamine (dropwise). Upon addition of 0.5 g. of 4-dimethylaminopyridine the mixture is stirred at room temperature overnight. The solution is refluxed for one hour and filtered. The solid is oven dried and partitioned between methylene chloride and water. The layers are separated and the organic phase dried over magnesium sulfate. The organic layer is concentrated and the residue collected and crystallized from cyclohexane and recrystallized from acetonitrile to yield the product.

Workup

  1. additionUpon addition of 0.5 g
  2. temperatureThe solution is refluxed for one hour
  3. filtrationfiltered
  4. customdried
  5. custompartitioned between methylene chloride and water
  6. customThe layers are separated
  7. dry with materialthe organic phase dried over magnesium sulfate
  8. concentrationThe organic layer is concentrated
  9. customthe residue collected
  10. customcrystallized from cyclohexane
  11. customrecrystallized from acetonitrile
  12. customto yield the product

Sources & evidence

ORD record
ord-74a655b02ddc4fdba4778b24155f1922
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Linked notes

Loading…