Sodium Carbonate → HCID 178488969, compound

HRID 235970Notes

Reaction equation

HRID 235970 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[NH:7][CH:8]=1)(=O)[NH2:2].C([O-])([O-])=O.[Na+].[Na+]>O=P(Cl)(Cl)Cl>[C:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[NH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 178488972HCID 178488972, compound

Product 1

HCID 178488969HCID 178488969, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 64 (7.6 g, 0.035 mol) and POCl3 (100 ml) was heated at reflux for 5.5 hours. After stirring at room temperature overnight, the suspension was poured into saturated Na2CO3 and the mixture extracted with 20% CH3OH--CHCl3 (3×). The organic extracts were washed with saturated NaCl, dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 5% CH3OH--CHCl3 to yield 5.0 g (71%) of 65; m.p. 219°-20° C. (CH3CN).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5.5 hours
  3. extractionthe mixture extracted with 20% CH3OH
  4. washThe organic extracts were washed with saturated NaCl
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was chromatographed on silica gel
  9. washthe product eluted with 5% CH3OH

Sources & evidence

ORD record
ord-db0d841ebcff40da8b8d546fb8cf9489
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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