Hydrochloric Acid → HCID 17866683, compound

HRID 583344Notes

Reaction equation

HRID 583344 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6](Br)[C:5]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[Cu][C:26]#[N:27].O.Cl>N1C=CC=CC=1>[C:26]([C:6]1[C:5]([NH:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)(=[O:15])=[O:14])=[C:4]([CH:9]=[C:8]([CH3:10])[CH:7]=1)[C:3]([OH:2])=[O:24])#[N:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 54067679HCID 54067679, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 17866683HCID 17866683, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4.0 g (10 mmol) of the product of Example 135 in 60 ml of pyridine was added 2.0 g (22 mmol) of copper (I) cyanide and the mixture was refluxed for 48 h. The reaction mixture was then cooled to room tempera and poured over cold water. The resulting mixture was stirred for sixteen hours and carefully acidified with concentted HCl solution. The resulting precipitate was filtered and washed with water, dissolved in chloroform, filtered and concentrated. The residue was triturated with ether, filtered and dried to provide 2.5 g (72%) of the desired product as a white solid. m.p. 162° C.; Electrospray Mass Spec 347 (M+H).

Workup

  1. temperaturethe mixture was refluxed for 48 h
  2. temperatureThe reaction mixture was then cooled to room tempera
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. dissolutiondissolved in chloroform
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-40669abfda2d4bbab2c697e8b8509b04
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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