Dimethylformamide → HCID 14989231, compound

HRID 1030924Notes

Reaction equation

HRID 1030924 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-55d321fb77064aca94d3934c10bd4d86
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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