Hydrochloric Acid → HCID 68410542, compound

HRID 859933Notes

Reaction equation

HRID 859933 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([C:15]([O-:17])=O)[C:10](OCC)=[O:11].[NH2:18][C:19]([NH2:21])=[S:20].[OH-].[Na+].[CH3:24]I.Cl>C1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]1[C:15](=[O:17])[NH:21][C:19]([S:20][CH3:24])=[N:18][C:10]1=[O:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 86612013HCID 86612013, compound

Product 1

HCID 68410542HCID 68410542, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8078CyclohexaneSolvent

Procedure

60.0 g (208 mmol) of ethyl 2-(2-chloro-6-fluorophenyl)malonate and 19.0 g (249 mmol) of thiourea were heated for 2.5 hours at 150° C. in 77 g (416 mmol) of n-tributylamine. Most of the ethanol formed was distilled off. 180 ml of an aqueous solution of 24.9 g (623 mmol) of NaOH were added to the reaction mixture once it had cooled down. After the aqueous phase had been treated with 50 ml of cyclohexane and stirred for approximately 30 minutes, it was separated off, treated with 35.4 g (142 mmol) of methyl iodide and stirred for approximately 16 hours at approximately 20 to 25° C. After acidification with dilute HCl solution and stirring for approximately 30 minutes, the precipitate was filtered off washing with water and drying gave 16.7 g of the title compound as white crystals of m.p. 250° C. (decomp.).

Workup

  1. distillationwas distilled off
  2. temperaturehad cooled down
  3. customit was separated off
  4. stirringstirred for approximately 16 hours at approximately 20 to 25° C
  5. filtrationthe precipitate was filtered off
  6. washwashing with water
  7. customdrying

Sources & evidence

ORD record
ord-5f79d6e605c44837b694a62ed130dcbc
Source dataset
uspto-grants-2006_12
Patent number
US07153860B2

Reaction notes

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