N-methyl-2-pyrrolidone → HCID 21476419, compound

HRID 440886Notes

Reaction equation

HRID 440886 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[Cu][C:23]#[N:24].[CH3:25][N:26]1CCCC1=O>>[C:25]([C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:23]#[N:24])=[CH:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1)#[N:26]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 214764092-(4-Bromobenzyl)-4-(4-bromophenyl)pyrimidineHCID 178418546HCID 178418546, compound

Product 1

HCID 21476419HCID 21476419, compound

Procedure

A mixture of 2-(4-bromobenzyl)-4-(4-bromophenyl)pyrimidine (8.8 g, 0.02 mole) and copper(I) cyanide (4.45 g, 0.05 mole) in 25 mL dry N-methyl-2-pyrrolidone is heated under nitrogen for 3-4 hr (TLC followed), during which time the color changes to dark brown. The mixture is poured into 250 mL ice cold water and a brown solid precipitated. The mixture is stirred for 2 hr with 200 mL of 10% NaCN solution; the solid is filtered, washed with water (1 L) and dried. The brown solid is placed in a soxlet device and treated with ethanol for 36 hr. The solvent is removed, the light brown solid chromatographed over neutral aluminumoxide, elution is with ether:CHCl3 (8:2) (20×50 mL fractions). Evaporation of the solvent yields a white solid which is dried in vacuo at 100° C. for 6-7 hr to give 2.3 g (39%), mp 155°-156° C.

Workup

  1. temperatureis heated under nitrogen for 3-4 hr (TLC followed)
  2. customa brown solid precipitated
  3. filtrationthe solid is filtered
  4. washwashed with water (1 L)
  5. customdried
  6. additiontreated with ethanol for 36 hr
  7. customThe solvent is removed
  8. customthe light brown solid chromatographed over neutral aluminumoxide, elution
  9. customEvaporation of the solvent
  10. customyields a white solid which
  11. customis dried in vacuo at 100° C. for 6-7 hr
  12. customto give 2.3 g (39%), mp 155°-156° C.

Sources & evidence

ORD record
ord-71035e366a2b4ccabc0082affb64c55d
Source dataset
uspto-grants-1996_05
Patent number
US05521189

Reaction notes

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