Water → 5-(Pyrid-2-yl)thiophene-2-carbonyl azide

HRID 857914Notes

Reaction equation

HRID 857914 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([C:12](Cl)=[O:13])=[CH:9][CH:8]=1.[N-:15]=[N+:16]=[N-:17].[Na+].O>CC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([C:12]([N:15]=[N+:16]=[N-:17])=[O:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 33557Sodium AzideHCID 27761995-(2-Pyridinyl)-2-thiophenecarbonyl chloride

Product 1

HCID 180051545-(Pyrid-2-yl)thiophene-2-carbonyl azideYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 5-(pyrid-2-yl)thiophene-2-carbonyl chloride (254 mg, Reference Example 43) in acetone (3 mL) was treated with a solution of sodium azide (128 mg) in a water and acetone mixture (3.5 mL, 1:6, v/v). After stirring at room temperature for a further 75 minutes the reaction mixture was treated with water (4 mL). The insoluble material was collected and washed with water to give the title compound (217 mg) as a white solid, which was used without further purification.

Workup

  1. customThe insoluble material was collected
  2. washwashed with water

Sources & evidence

ORD record
ord-c6168466f14f4f0083bd7ed9296f91d9
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

Loading…