Sodium Azide → Isopropyl 5-(2-azidoethyl)thiophene-2-carboxylate

HRID 1528014Notes

Reaction equation

HRID 1528014 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])=[CH:10][CH:9]=1>CN(C=O)C.CCOC(C)=O>[N:1]([CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14])=[CH:10][CH:9]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57487061Isopropyl 5-(2-bromoethyl)thiophene-2-carboxylate

Product 1

HCID 57487064Isopropyl 5-(2-azidoethyl)thiophene-2-carboxylateYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (697 mg, 10.7 mmol) was added to a solution of the bromide from step 2 (2.7 g, 9.7 mmol) in DMF (39 mL) at room temperature. After 18 h at room temperature, the reaction mixture was diluted with EtOAc (300 mL) and washed with water (3×100 mL) and brine (50 mL). The organic phases was dried (Na2SO4), filtered and concentrated in vacuo to afford 2.24 g (96%) of isopropyl 5-(2-azidoethyl)thiophene-2-carboxylate.

Workup

  1. washwashed with water (3×100 mL) and brine (50 mL)
  2. dry with materialThe organic phases was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-836ce55805a049219c3e3828d895bc59
Source dataset
uspto-grants-2015_07
Patent number
US09090584B2

Reaction notes

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