Potassium Hydroxide → HCID 53856080, compound

HRID 1636878Notes

Reaction equation

HRID 1636878 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[C:5]([CH3:14])[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[OH-].[K+]>CCO.O.CCOCC.[Cl-].[Na+].O>[CH3:13][C:10]([O:9][C:7]([C:6]1[C:5]([CH3:14])=[C:4]([C:15]([OH:17])=[O:16])[S:3][C:2]=1[NH2:1])=[O:8])([CH3:11])[CH3:12]

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 10882569HCID 10882569, compound

Product 1

HCID 53856080HCID 53856080, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a cold degassed solution of the compound prepared in Example 2 (22.6 g, 64.9 mmol) in EtOH (700 ml) was added 3M KOH (350 ml) dropwise over 30 minutes. When the addition was complete the reaction was warmed to room temperature. After 3 days the reaction was diluted with H2O, Et2O and brine. The layers were separated and the aqueous layer was further extracted with Et2O (2×). The combined Et2O layers were extracted with 0.1M KOH (1×). All of the aqueous basic layers were combined and cooled to 15° C. and acidified dropwise with 3M HCl (aq) (note: do not let the internal temperature rise above 18° C.).

Workup

  1. additionWhen the addition
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with Et2O (2×)
  4. extractionThe combined Et2O layers were extracted with 0.1M KOH (1×)
  5. temperaturecooled to 15° C.
  6. customthe internal temperature rise above 18° C.

Sources & evidence

ORD record
ord-7a66bc43293747728c214b94751b9916
Source dataset
uspto-grants-2000_03
Patent number
US06037340

Reaction notes

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