Hydrochloric Acid → HCID 54236563, compound

HRID 429179Notes

Reaction equation

HRID 429179 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH:6]1([NH:12][C:13](=[O:24])[CH2:14][CH2:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][CH2:14][C:13]([NH:12][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:24])=[S:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723789ThiosemicarbazideHCID 18523497HCID 18523497, compound

Product 1

HCID 54236563HCID 54236563, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (1.75 g, 19.2 mmol) was added to a solution of N-cyclohexyl-4-oxo-4-phenyl-butyramide (3.30 g, 11.7 mmol), prepared in the previous step, in 40 ml of methanol plus 3.2 ml of 1 N HCl plus 3.2 ml of water and the reaction stirred at room temperature for 21 hours. The solid formed was removed by filtration and dried to give 2.69 g of a white solid. The filtrate was concentrated under reduced pressure to remove the methanol. The residue was partitioned between methylene chloride and water. The organic layer was separated, washed multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 1.10 g of a white foam. The initial solid filtered from the reaction was dissolved in methylene chloride, washed multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give a white foam. Both materials were combined and crystallized from methylene chloride-ethyl acetate to give the title compound (3.31 g, 69%) as a white solid, mp 89-92° C.

Workup

  1. customThe solid formed
  2. customwas removed by filtration
  3. customdried

Sources & evidence

ORD record
ord-cac83746edb447a9b31a1c8a924419e6
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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