Ozone → HCID 10011933, compound

HRID 1492964Notes

Reaction equation

HRID 1492964 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=CC2C=CC=CC=2)[N:4]=1)#[N:2].[O:17]=[O+][O-]>CO.C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=[O:17])[N:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 24823Ozone2×HCID 53759438HCID 53759438, compound

Product 1

HCID 10011933HCID 10011933, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2.238 g (10.81 mmol) of 4-cyano-2-(2-phenylethenyl)-pyrimidine in 150 ml of absolute methanol and 75 ml of absolute methylene chloride are cooled to -70° C. Ozone is passed through until a blue solution is produced (about 0.5 hour). Nitrogen is passed through the solution until the excess ozone has been removed (about 0.75 hour) and then 3.5 ml of dimethyl sulfide are added to the reaction mixture. The solution is allowed to warm up to room temperature and is concentrated in a rotary evaporator. The crude product is purified over silica gel (eluant: n-hexane/ethyl acetate 1:3). 1H-NMR (CDCl3): δ=10.11 (s, 1H); 9.23 (d, 1H); 7.82 (d, 1H).

Workup

  1. customis produced (about 0.5 hour)
  2. customhas been removed (about 0.75 hour)
  3. addition3.5 ml of dimethyl sulfide are added to the reaction mixture
  4. concentrationis concentrated in a rotary evaporator
  5. customThe crude product is purified over silica gel (eluant: n-hexane/ethyl acetate 1:3)

Sources & evidence

ORD record
ord-8b067d135b7f4e518e3c6c022ae0ae5c
Source dataset
uspto-grants-1994_12
Patent number
US05376685

Reaction notes

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