Hexane → HCID 136182254, compound

HRID 425767Notes

Reaction equation

HRID 425767 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]3[S:15][C:14](SC)=[N:13][C:12]3=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1.CC(C)([O-])C.[K+].CCCCCC.[N:31]#[C:32][NH2:33].[OH-].[K+].[K]>CN1C(=O)CCC1.O.CCOC(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]3[S:15][C:14](=[N:33][C:32]#[N:31])[NH:13][C:12]3=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

10

Reactant 6

HCID 8058HexaneHCID 9864CyanamideHCID 14797Potassium HydroxideHCID 677048HCID 677048, compoundHCID 5462222PotassiumHCID 23665647Potassium tert-butoxide

Product 1

HCID 136182254HCID 136182254, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

200 mg (0.72 mmol) of 5-Benzo[1,3]dioxol-5-ylmethylene-2-methylsulfanyl-thiazol-4-one were dissolved in NMP to which was added a solution of potassium tert.butoxide in hexane (1.1 eq.). The colour changed to orange. To this was added as a solid cyanamide (1.2 eq.). The reaction was heated at 80° C. under Ar. for 3 h HPLC indicated complete transformation. 150 ml EtOAc were added and washed with 0.1N HCl twice. The organic layer was then washed extensively with brine. The solvent was dried and evaporated to dryness leading to a yellowish solid. The crude was purified on Parallel Flex system affording a yellow solid, which was dissolved in TBF followed by 1 equivalent of 1N KOH. 20 ml of water were added and the frozen solution was lyophilised yielding 107 mg (51%) of 5-Benzo[1,3]dioxol-5-ylmethylene-4-oxo-thiazolidin-2-ylidene-cyanamide as potassium salt.

Workup

  1. washwashed with 0.1N HCl twice
  2. washThe organic layer was then washed extensively with brine
  3. customThe solvent was dried
  4. customevaporated to dryness
  5. customThe crude was purified on Parallel Flex system
  6. customaffording a yellow solid, which
  7. dissolutionwas dissolved in TBF

Sources & evidence

ORD record
ord-000bb9c78c9e493f880f6b263c11f317
Source dataset
uspto-grants-2012_01
Patent number
US08106214B2

Reaction notes

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