Dimethylformamide → HCID 10936494, compound

HRID 233291Notes

Reaction equation

HRID 233291 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23]Br)=[CH:17][CH:16]=1.[C-]#N.[K+].[CH3:28][N:29](C)C=O>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][C:28]#[N:29])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 10894343HCID 10894343, compound

Product 1

HCID 10936494HCID 10936494, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propyl bromide (1.5 g), powdered potassium cyanide (1.52 g) and N,N-dimethylformamide (30 ml) was stirred for 3 hours at 80° C. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), which was then concentrated to give 4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]butyronitrile (1.2 g, 92%). Recrystallization of the product from ethyl acetate--hexane gave colorless needles, m.p.73°-74° C.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4), which
  4. concentrationwas then concentrated

Sources & evidence

ORD record
ord-962f9b03bc0c4e0689055f57915a1bf5
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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