Dimethylformamide → HCID 178418411, compound

HRID 2393721Notes

Reaction equation

HRID 2393721 reaction equation
Br[CH2:2][CH2:3]Br.[N-:5]=[N+:6]=[N-:7].[Na+].[N-]=[N+:10]=[N-:11].[Li][CH3:13].C[N:15]([CH:17]=O)C>>[CH3:13][NH:5][N:6]=[N:7][CH2:2][CH2:3][N:10]=[N:11][NH:15][CH3:17]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 33557Sodium AzideHCID 33558AzideHCID 178418348HCID 178418348, compound

Product 1

HCID 178418411HCID 178418411, compoundYield 32%

Conditions

Temperature
50 °C

Procedure

A flask is charged with 5.0 g (27 mmole) of 1,2-dibromoethane, 3.8 g (58 mmole) of sodium azide, and 50 ml of DMF. The mixture is heated at 50° C. with stirring under argon overnight. The mixture is worked up as described above, except that the azide solution is not evaporated down totally. When about 30 ml of solution remains the mixture is treated with 45 ml of a 1.3M solution of MeLi (58 mmole) as above. After 3 hr the reaction is worked up as described above, and a yellow solid is obtained. Crystallization from ether/petroleum ether affords 1.23 g (32% yield) of an off-white solid, mp 64°-6° C. Mass spectra (FAB) Calc (M+H) 145.1201, Found 145.1220±0.0015.

Workup

  1. customis not evaporated down totally
  2. waitAfter 3 hr the reaction is worked up
  3. customis obtained
  4. customCrystallization from ether/petroleum ether

Sources & evidence

ORD record
ord-d41df6312e2d4672b3025433ac58eee6
Source dataset
uspto-grants-1998_09
Patent number
US05808038

Reaction notes

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