Hydrochloric Acid → HCID 68528646, compound

HRID 1929540Notes

Reaction equation

HRID 1929540 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.[CH3:20][C:21]1([CH3:29])[CH2:26][C:25](=[O:27])[CH2:24][C:23](=O)[CH2:22]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:24]2[C:25](=[O:27])[CH2:26][C:21]([CH3:29])([CH3:20])[CH2:22][C:23]=2[NH:8]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 31358DimedoneHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 186795841,3-Thiazole-2-carboximidamide hydrochloride

Product 1

HCID 68528646HCID 68528646, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-thiazolecarboxamidine hydrochloride (Schaefer F. C., Peters G. A., et al.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 5,5-dimethyl-1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under refluxing for 18 hr, condensed, to which ethyl acetate and water and 1N HCl were added, and separated. The water layer was adjusted with concentrated NaOH solution until pH value to be basic, then ethyl acetate was added and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain a yellow crystal 0.23 g (yield 28%); 1H-NMR (400 MHz, CDCl3-d1) δ 7.95-7.85 (m, 1H, ArH); 7.64-7.47 (m, 1H, ArH); 7, 34-7.24 (m, 1H, ArH); 7.13-7.11 (m, 1H, ArH); 6.11 (s, 1H, CH); 2.70-2.52 (m, 2H, CH2); 2.43-2.26 (m, 2H, CH2); 1.15 (s, 6H, CH3). HREI: 389.0765 (M+).

Workup

  1. temperatureunder refluxing for 18 hr
  2. customcondensed
  3. customseparated
  4. additionethyl acetate was added
  5. extractionextracted twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. customseparated by column chromatography

Sources & evidence

ORD record
ord-36046b5b25c04ceabfeb4fd924006c24
Source dataset
uspto-grants-2012_05
Patent number
US08188091B2

Reaction notes

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