Sodium Iodide → N'-{4-[1-(4-chlorophenyl)cyclobutyl]thiazol-2-yl}-N,N-diethylpropane-1,3-diamine

HRID 47271Notes

Reaction equation

HRID 47271 reaction equation
Cl[CH2:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=O.[I-].[Na+].[CH2:18]([N:20]([CH2:28][CH3:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH2:27])=[S:26])[CH3:19]>CC(C)=O.C(=O)([O-])O.[Na+].O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2([C:3]3[N:27]=[C:25]([NH:24][CH2:23][CH2:22][CH2:21][N:20]([CH2:18][CH3:19])[CH2:28][CH3:29])[S:26][CH:2]=3)[CH2:8][CH2:7][CH2:6]2)=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 3034968Pseudourea, 3-(diethylaminopropyl)-2-thio-HCID 219020652-Chloro-1-[1-(4-chlorophenyl)cyclobutyl]ethanone

Product 1

HCID 21992323N'-{4-[1-(4-chlorophenyl)cyclobutyl]thiazol-2-yl}-N,N-diethylpropane-1,3-diamineYield 86.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-chloro-1-[1-(4-chlorophenyl)cyclobutyl]ethanone (120 mg, 0.494 mmol) and sodium iodide (74 mg, 0.494 mmol) in acetone (2.5 mL) was stirred at room temperature for 5 minutes. Next (3-diethylaminopropyl)thiourea (94 mg, 0.494 mmol) was added. The resulting mixture was heated at 50° C. for 1 h. After the mixture was allowed to cool to room temperature, it was diluted with 5% sodium hydrogen carbonate in water and then extracted with ethyl acetate (2×50 mL). The extracts were combined, washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give a colorless oil. The oil was purified by column chromatography on silica gel using dichloromethane/2 N ammonia in ethanol (90:10) to give 162 mg of N′-{4-[1-(4-chlorophenyl)cyclobutyl]thiazol-2-yl}-N,N-diethylpropane-1,3-diamine, 19, as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 1.02 (t, 6H, J=7.2 Hz); 1.71-1.80 (m, 2H); 1.82-1.91 (m, 1H); 2.08-2.20 (m, 1H); 2.48-2.59 (m, 8H); 2.67-2.76 (m, 2H); 3.27 (t, 2H, J=6.3 Hz); 5.91 s (s, 1H); 6.17 (bs, 1H); 7.25 (s, 4H); 13C NMR (CDCl3, 75 MHz): δ 11.8, 16.9, 26.2, 34.3, 45.8, 47.1, 49.1, 51.9, 100.3, 128.2, 128.3, 131.5, 147.1, 159.8, 169.9.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washwashed with brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. customThe oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-08e4b4dc0fd248899b47f0f6996da4a7
Source dataset
uspto-grants-2004_03
Patent number
US06699866B2

Reaction notes

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