Octanoyl chloride → HCID 178442555, compound

HRID 1171447Notes

Reaction equation

HRID 1171447 reaction equation
[C:1](Cl)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:11][NH:12][C:13](=[S:16])[NH:14][NH2:15].[OH-].[K+]>O1CCCC1>[CH2:2]([C:1]1[N:12]([CH3:11])[C:13]([SH:16])=[N:14][N:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8124Octanoyl chlorideHCID 14797Potassium HydroxideHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 178442555HCID 178442555, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g (30.74 mmol, 1 eq) of octanoyl chloride and 3.58 g (33.81 mmol, 1.1 eq) of 4-methyl-3-thiosemicarbazide in solution in 350 ml of tetrahydrofuran are stirred for 3 hours at room temperature. The solution is concentrated to dryness. The solid obtained is taken up in 350 ml of a 10% aqueous potassium hydroxide solution 35 g (0.82 mmol, 20 eq). The reaction mixture is stirred overnight under reflux. In the cold state, the reaction medium is acidified. The precipitate obtained is filtered, washed with a minimum of water and then dried. 5.94 g (90%) of the expected compound are obtained.

Workup

  1. concentrationThe solution is concentrated to dryness
  2. customThe solid obtained
  3. temperatureunder reflux
  4. customThe precipitate obtained
  5. filtrationis filtered
  6. washwashed with a minimum of water
  7. customdried

Sources & evidence

ORD record
ord-4ccef557b0134e728b4a16cff9905cf2
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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