1,2-Dibromoethane → 1-(2-Bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one

HRID 256644Notes

Reaction equation

HRID 256644 reaction equation
[Br:1][CH2:2][CH2:3]Br.C(=O)([O-])[O-].[Na+].[Na+].[CH2:11]([N:13]1[C:17](=[O:18])[NH:16][N:15]=[N:14]1)[CH3:12]>CN(C)C=O.O>[Br:1][CH2:2][CH2:3][N:16]1[C:17](=[O:18])[N:13]([CH2:11][CH3:12])[N:14]=[N:15]1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 10340Sodium CarbonateHCID 1354729431-ethyl-1,2-dihydro-5H-tetrazol-5-one

Product 1

HCID 30199151-(2-Bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-oneYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 109 parts of 1,2-dibromoethane and 21.2 parts of sodium carbonate in 5 parts of water and 18 parts of N,N-dimethylformamide were added dropwise a solution of 22.5 parts of 1-ethyl-1,4-dihydro-5H-tetrazol-5-one in 5 parts of water and 27 parts of N,N-dimethylformamide at about 40° C. Upon completion, stirring was continued overnight at 40° C. The organic phase was separated, dried and distilled, yielding 9.8 parts (22%) of 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one; bp. 110° C. at 0.1 mm pressure (interm. 47).

Workup

  1. customThe organic phase was separated
  2. customdried
  3. distillationdistilled

Sources & evidence

ORD record
ord-20708674406f4c59b85b19653fc5802e
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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