Hydrochloric Acid → HCID 22325509, compound

HRID 496304Notes

Reaction equation

HRID 496304 reaction equation
[C:1]1([CH:7]([C:13]([O-:15])=O)[C:8](OCC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][C:17]([NH2:19])=[S:18].[CH2:20](N(CCCC)CCCC)CCC.[OH-].[Na+].CI.Cl>C1CCCCC1.C(O)C>[C:1]1([CH:7]2[C:13](=[O:15])[NH:19][C:17]([S:18][CH3:20])=[N:16][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 7622TributylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 21953396HCID 21953396, compound

Product 1

HCID 22325509HCID 22325509, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8078CyclohexaneSolvent

Procedure

60.0 g (208 mmol) of ethyl 2-phenylmalonate and 19.0 g (249 mmol) of thiourea were heated at 150° C. for 2.5 hours in 77 g (416 mmol) of tri-n-butylamine. The resultant ethanol was for the most part distilled off. After the reaction solution had cooled, 180 ml of an aqueous solution of 24.9 g (623 mmol) of NaOH were added to it. After adding 50 ml of cyclohexane and stirring for about 30 min the aqueous phase was separated off, treated with 35.4 g (142 mmol) of methyl iodide and stirred at approximately 20 to 25° C. for about 16 h. After acidification with dilute HCl solution and stirring for about 30 min the precipitate was filtered off. After washing with water and drying, 16.7 g of the compound in the title (28% of theoretical) were obtained in the form of white crystals.

Workup

  1. distillationdistilled off
  2. temperatureAfter the reaction solution had cooled
  3. customwas separated off
  4. stirringstirred at approximately 20 to 25° C. for about 16 h
  5. filtrationwas filtered off
  6. washAfter washing with water
  7. customdrying

Sources & evidence

ORD record
ord-612b5d2e84164123b70ee172817092b1
Source dataset
uspto-grants-2005_09
Patent number
US06943252B2

Reaction notes

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