Carbon Disulfide → HCID 178527933, compound

HRID 1369635Notes

Reaction equation

HRID 1369635 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16]([NH:18][NH2:19])=[O:17])=[CH:15][C:8]=23)=[CH:4][CH:3]=1.[C:22](=S)=[S:23].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16]4[O:17][C:22]([SH:23])=[N:19][N:18]=4)=[CH:15][C:8]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 9966826HCID 9966826, compound

Product 1

HCID 178527933HCID 178527933, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

The compound from Example 156 (100 mg, 0.31 mmol) was suspended in ethanol (2 ml) and cooled to 0° C. Carbon disulfide (0.04 ml, 0.71 mmol) was added follow by potassium hydroxide (20 mg, 0.31 mmol). The reaction was stirred 1 hr and the cold bath removed. After 1 hr at ambient temperature, the reaction was refluxed for 3 hours then concentrated to a solid. The crude solid was triturated with chloroform (1×5 ml) and concentrated. The residue was dissolved in water (15 ml) and acidified with formic acid. The resulting precipitate was isolated by filtration, washed with water (2×15 ml), and dried in a desiccator to yield the title compound (106 mg, 94%).

Workup

  1. customthe cold bath removed
  2. waitAfter 1 hr at ambient temperature
  3. temperaturethe reaction was refluxed for 3 hours
  4. concentrationthen concentrated to a solid
  5. customThe crude solid was triturated with chloroform (1×5 ml)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in water (15 ml)
  8. customThe resulting precipitate was isolated by filtration
  9. washwashed with water (2×15 ml)
  10. customdried in a desiccator

Sources & evidence

ORD record
ord-f5282a87dffc4ddc84e58ea0f1911dd6
Source dataset
uspto-grants-2003_06
Patent number
US06579882B2

Reaction notes

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