Dimethylformamide → HCID 14989231, compound

HRID 981643Notes

Reaction equation

HRID 981643 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].Cl.[O:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:10]1[CH2:14][CH2:13][N:12]=[C:11]1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 810936-BromohexanenitrileHCID 136404539HCID 136404539, compound

Product 1

HCID 14989231HCID 14989231, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-bromohexanenitrile, 12 parts of 4-(2-oxazolyl)phenol monohydrochloride, 16.6 parts of potassium carbonate and 282 parts of N,N-dimethylformamide was stirred overnight at 60° C. After cooling, the reaction mixture was poured into water and the product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.2 parts (20.6%) of 6-[4-(4,5-dihydro-2-oxazolyl)phenoxy]hexanenitrile (int. 107).

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with methylbenzene
  3. washThe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 2,2'-oxybispropane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-b6753cf66c414250b913936c7240984f
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

Loading…