HCID 178418361, compound → HCID 178425411, compound

HRID 2108178Notes

Reaction equation

HRID 2108178 reaction equation
[H][H].Br[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][S:12]([C:15]2[N:19]=[C:18]([NH:20]C=O)[NH:17][N:16]=2)(=[O:14])=[O:13])=[C:6]([Cl:23])[C:5]=1[CH3:24]>C(O)C>[Cl:23][C:6]1[C:5]([CH3:24])=[CH:4][CH:9]=[C:8]([Cl:10])[C:7]=1[NH:11][S:12]([C:15]1[N:19]=[C:18]([NH2:20])[NH:17][N:16]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178421698HCID 178421698, compound

Product 1

HCID 178425411HCID 178425411, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 3-necked flask equipped with a thermometer, reflux condenser with a nitrogen outlet, a sparge tube to introduce hydrogen and a spinbar was charged with the product of Example 11 (2 g, 4.66 mmol) and 100 mL of 95% ethanol. The mixture was stirred rapidly and purged with nitrogen and 150 mg of 10% Pd/C was added. Hydrogen gas was bubbled through the mixture while heating to reflux. After three hr of reflux the reaction was essentially complete. The mixture was purged with nitrogen and filtered. The filtrate was concentrated to yield the title compound as an off white solid, 1.5 g (98%) m.p. 198°-200° C.

Workup

  1. customA 3-necked flask equipped with a thermometer
  2. temperaturereflux condenser with a nitrogen outlet, a sparge tube
  3. custompurged with nitrogen and 150 mg of 10% Pd/C
  4. additionwas added
  5. customHydrogen gas was bubbled through the mixture
  6. temperaturewhile heating to reflux
  7. temperatureAfter three hr of reflux the reaction
  8. customThe mixture was purged with nitrogen
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ff05bc16a5d14c48b94a05493c01a827
Source dataset
uspto-grants-1990_06
Patent number
US04937350

Reaction notes

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