Hydrochloric Acid → HCID 68525469, compound

HRID 1929541Notes

Reaction equation

HRID 1929541 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([NH2:9])=[NH:8].[Cl:10][C:11]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:12]=1[CH:13]=O.[C:20]1(=O)[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH2:21]1.C([O-])(=O)C.[Na+].Cl>C(O)C.O.C(OCC)(=O)C>[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[N:9]=[C:13]([C:12]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:11]=2[Cl:10])[C:21]2[C:22](=[O:26])[CH2:23][CH2:24][CH2:25][C:20]=2[NH:8]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 104341,3-CyclohexanedioneHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 186795841,3-Thiazole-2-carboximidamide hydrochloride

Product 1

HCID 68525469HCID 68525469, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-thiazolecarboxamidine hydrochloride (Schaefer P. C., Peters G. A., et al.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml anhydrous ethanol under refluxing for 18 hr, and condensed, to which ethyl acetate and water and 1N HCl were added and the layers were separated. The water layer was adjusted with concentrated NaOH solution until pH value to be basic, then ethyl acetate was added again and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain a yellow crystal of 0.21 g (yield 27%); 1H-NMR (400 MHz, CDCl3-d1) δ 7.86 (m, 1H, ArH); 7.73-7.52 (m, 1H, ArH); 7.24-7.21 (m, 1H, ArH); 7.15-7.12 (m, 1H, ArH); 6.94-6.92 (m, 1H, ArH); 6.11 (s, 1H, CH); 2.80-2.47 (m, 2H, CH2); 2.14-2.11 (m, 2H, CH2). HREI: 361.0450 (M+).

Workup

  1. temperatureunder refluxing for 18 hr
  2. customcondensed
  3. customthe layers were separated
  4. additionethyl acetate was added again
  5. extractionextracted twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. customseparated by column chromatography
  8. customto obtain a yellow crystal of 0.21 g (yield 27%)

Sources & evidence

ORD record
ord-61e4e8b1f5b345af81ff6ecf57753b8c
Source dataset
uspto-grants-2012_05
Patent number
US08188091B2

Reaction notes

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