Water → HCID 22314782, compound

HRID 1634040Notes

Reaction equation

HRID 1634040 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.Br[CH2:11][CH2:12]Br.[NH2-].[Na+].[OH2:16].C(Cl)[Cl:18]>>[ClH:18].[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2([C:8]([NH2:9])=[O:16])[CH2:12][CH2:11]2)[CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 78391,2-DibromoethaneHCID 24533Sodium amideHCID 41120852-(Pyridin-4-yl)acetonitrile

Product 1

HCID 22314782HCID 22314782, compound

Procedure

3.5 g of pyridin-4-ylacetonitrile and then 2.6 ml of 1,2-dibromoethane are added to a mixture of 2.5 g of sodium amide in 80 ml of DCM and the mixture is left stirring overnight at RT. The reaction mixture is poured into water, extracted with AcOEt, the organic phase washed with water, dried over Na2SO4 and the solvents evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with DCM and then with the DCM/MeOH mixture from (99/1; v/v) to (95/5; v/v). 2.5 g of the expected product are obtained.

Workup

  1. waitthe mixture is left
  2. extractionextracted with AcOEt
  3. washthe organic phase washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvents evaporated off under vacuum
  6. customThe residue is chromatographed on silica gel
  7. washeluting with DCM

Sources & evidence

ORD record
ord-2076f4e2a05a4ff5a2c58f4d15703374
Source dataset
uspto-grants-2003_01
Patent number
US06506750B1

Reaction notes

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