2-Nitropropane → HCID 12401526, compound

HRID 1763939Notes

Reaction equation

HRID 1763939 reaction equation
[N+](C(C)C)([O-])=[O:2].[Na].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:24]=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]3[N:17]=2)=[CH:12][CH:11]=1>C(O)C.CN(C)C=O>[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:24]=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]3[N:17]=2)=[CH:12][CH:11]=1)=[O:2]

Participants

6

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 12401525HCID 12401525, compound

Product 1

HCID 12401526HCID 12401526, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

11.6 g of 2-nitropropane are introduced at about 30° C. into a solution of 2.3 g of sodium in 450 ml of absolute ethanol. The mixture is stirred for a further 1 hour and a solution of 28.8 g of 2-(p-bromomethyl-phenyl)-s-triazolo[1,5-a]pyridine (I) in 290 ml of dimethylformamide is now added. Subsequently, the reaction mixture is warmed to 50° C., then stirred for 20 hours without external warming and finally cooled to -10° C. The product which has precipitated is filtered off, washed with cold methanol and dried. This gives 19.3 g (86.5% of theory) of compound (II) in the form of a pale yellow powder with a melting point of 243° to 244° C. After recrystallising twice from dimethylformamide, 14.67 g (65.7% of theory) of small, virtually colourless, glossy needles with a melting point of 246° to 247° C. are obtained.

Workup

  1. stirringstirred for 20 hours
  2. temperaturewithout external warming
  3. temperaturefinally cooled to -10° C
  4. customThe product which has precipitated
  5. filtrationis filtered off
  6. washwashed with cold methanol
  7. customdried
  8. customAfter recrystallising twice from dimethylformamide, 14.67 g (65.7% of theory) of small, virtually colourless, glossy needles with a melting point of 246° to 247° C.
  9. customare obtained

Sources & evidence

ORD record
ord-db9753bbc01042188bf6151703c27a4a
Source dataset
uspto-grants-1978_09
Patent number
US04113937

Reaction notes

Loading…