Hydrochloric Acid → HCID 53954178, compound

HRID 1004486Notes

Reaction equation

HRID 1004486 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].O=[C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:8][NH:9][C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:8][NH:9][C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])=[S:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723789ThiosemicarbazideHCID 54070217HCID 54070217, compound

Product 1

HCID 53954178HCID 53954178, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (2.23 g, 24.5 mmol) was added to a solution of cyclohexane carboxylic acid (2-oxo-2-phenyl-ethyl)-amide (6.0 g, 24.5 mmol), prepared in the previous step, in 87 ml of methanol plus 6.75 ml of 1N HCl plus 6.25 ml of water and the reaction stirred at room temperature for 4 days. The solvent was removed under reduced pressure to give 8.2 g of a green oil which was chromatographed on 400 g of silica gel (230-400 mesh) using ethyl acetate-methylene chloride as the eluent. The material isolated was recrystallized from isopropyl alcohol to give the title compound (3.55 g, 46%) as a white solid, mp 104-110° C.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-97a4cb71253947b7b00c6e6eb60b4fa5
Source dataset
uspto-grants-2000_04
Patent number
US06049006

Reaction notes

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