Water → HCID 178505665, compound

HRID 1097648Notes

Reaction equation

HRID 1097648 reaction equation
[Cl-].C([NH+](CC)CC)C.[N-:9]=[N+:10]=[N-:11].[Na+].[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=1.O>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[NH:22][N:11]=[N:10][N:9]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 12698378Triethylazanium chloride

Product 1

HCID 178505665HCID 178505665, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of triethylammonium chloride (4.14 g, 30 mmol) and sodium azide (1.95 g, 30 mmol) was treated with a solution of (4-fluorophenyl)acetonitrile (1.35 g, 10 mmol) in toluene (14 ml) and the mixture was stirred and heated at 100° C. for 5 h. The cooled mixture was treated with water (10 ml) and the mixture separated. The aqueous phase was stirred and treated dropwise with concentrated hydrochloric acid until the product had precipitated from solution. The precipitated product was filtered off, washed with water and dried to yield the title compound as a white solid (1.27 g, 72%).

Workup

  1. customthe mixture separated
  2. stirringThe aqueous phase was stirred
  3. additiontreated dropwise with concentrated hydrochloric acid until the product
  4. customhad precipitated from solution
  5. filtrationThe precipitated product was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-303c72597ca04040ba8a0fa027a0e3b6
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

Loading…