N-methyl-2-pyrrolidone → HCID 54149628, compound

HRID 1076658Notes

Reaction equation

HRID 1076658 reaction equation
C[N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.P(Cl)(Cl)(Cl)=O.[N+:13]([C:16]1[O:20][C:19]([C:21]2[N:26]=[C:25]([NH:27][NH2:28])[CH:24]=[CH:23][N:22]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14].O1CCOC[CH2:30]1>>[CH3:30][N:28]([N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1)[NH:27][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([C:19]2[O:20][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)[N:26]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24813Phosphorus oxychlorideHCID 312751,4-Dioxane2×HCID 21537469HCID 21537469, compound

Product 1

HCID 54149628HCID 54149628, compound

Procedure

2.08 ml. 1-methyl-2-pyrrolidone were dissolved in 8.6 ml. anhydrous dioxan, 1.92 ml. phosphorus oxychloride were added dropwise and the mixture was stirred for 1 hour at 25° - 30°C. 2.2 g. 2-(5-nitro-2-furyl)-4-hydrazino-pyrimidine were then added, a further 6.2 ml. anhydrous dioxan were added and the reaction mixture stirred for 1.5 hours at 30° - 35°C. The reaction mixture was then poured on to ice, filtered with activated charcoal and neutralized with a dilute aqueous solution of ammonia. There were thus obtained 2.6 g. (87% of theory) of a red-brown product, which was recrystallized from dioxan. There was thus obtained 1-methyl-2-[2-(5-nitro-2-furyl)-4-pyrimidinyl]-hydrazino-pyrrolidine, which melted at 175° - 177°C. The spectral and elementary analysis confirmed the structure.

Workup

  1. stirringthe reaction mixture stirred for 1.5 hours at 30° - 35°C
  2. additionThe reaction mixture was then poured on to ice
  3. filtrationfiltered with activated charcoal
  4. custom(87% of theory) of a red-brown product, which was recrystallized from dioxan

Sources & evidence

ORD record
ord-1766b91f7f9c4ebfa995e88080df65a1
Source dataset
uspto-grants-1976_05
Patent number
US03957766

Reaction notes

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