Butyryl chloride → HCID 178440341, compound

HRID 1885103Notes

Reaction equation

HRID 1885103 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([NH:18][NH2:19])=O)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[C:20](Cl)(=O)[CH2:21][CH2:22][CH3:23].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>N1C=CC=CC=1.C1COCC1>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[S:35][C:20]([CH2:21][CH2:22][CH3:23])=[N:19][N:18]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 8855Butyryl chlorideHCID 87949Lawesson's reagentHCID 178448071HCID 178448071, compound

Product 1

HCID 178440341HCID 178440341, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.25 mol of trans-4-(trans-4-n-propylcyclohexyl)cyclohexanecarbohydrazide is dissolved in 300 ml of pyridine. At room temperature, 0.25 mol of butyryl chloride is added dropwise, and the mixture is stirred for a further 11/2 hours. The mixture is then poured into 1.5 1 of ice/water, and the crystals are filtered off with suction and washed with water. The product obtained is recrystallized from toluene. 0.1 mol of this compound and 0.1 mol of Lawesson's reagent are refluxed for 10 hours in 200 ml of THF. 2/3 of the solvent are removed by distillation, the residue is poured into 500 ml of water and 50 ml of 32% sodium hydroxide solution, and the precipitate is filtered off with suction and recrystallized from ethanol/activated charcoal to give 2-[trans-4-(trans-4-n-propylcyclohexyl)cyclohexyl]-5-propyl-1,3,4-thiadiazole.

Workup

  1. filtrationthe crystals are filtered off with suction
  2. washwashed with water
  3. customThe product obtained
  4. customis recrystallized from toluene
  5. custom2/3 of the solvent are removed by distillation
  6. additionthe residue is poured into 500 ml of water and 50 ml of 32% sodium hydroxide solution
  7. filtrationthe precipitate is filtered off with suction
  8. customrecrystallized from ethanol/activated charcoal

Sources & evidence

ORD record
ord-63332dc128384324875588e4d7dcc5fb
Source dataset
uspto-grants-1992_09
Patent number
US05143642

Reaction notes

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