Triethylamine → HCID 21103259, compound

HRID 1354087Notes

Reaction equation

HRID 1354087 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH:14]2[C:28]([O:30][CH3:31])=[O:29])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+].CCN(CC)CC.[Cl:49][C:50]1[CH:58]=[CH:57][C:53]([C:54](Cl)=[O:55])=[CH:52][CH:51]=1>CO>[Cl:49][C:50]1[CH:58]=[CH:57][C:53]([C:54]([NH:1][C:4]2[CH:9]=[CH:8][C:7]([S:10]([N:13]3[CH2:18][C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH:14]3[C:28]([O:30][CH3:31])=[O:29])(=[O:12])=[O:11])=[CH:6][CH:5]=2)=[O:55])=[CH:52][CH:51]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 21103276HCID 21103276, compound

Product 1

HCID 21103259HCID 21103259, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The compound of Example 56 (0.55 g, 1.2 mmol) was put into 10 mL of a MeOH solution to which SnCl2.2H2O (1.1 g, 4.8 mmol) was added, and stirred for 1 hour while maintaining the temperature at 50° C. A saturated NaHCO3 aqueous solution was introduced and the mixture was stirred for 1 hour, and then it was extracted with ethyl acetate. After distillation under reduced pressure and vacuum drying, the mixture was dissolved in 20 mL of dichloromethane and Et3N (0.41 mL, 2.9 mmol), and 4-chlorobenzoyl chloride (0.31 mL, 2.4 mmol) was added while maintaining the temperature at 0° C. After reaction for 6 hours, the reactant was washed with a saturated NaHCO3 aqueous solution and a 1N HCl aqueous solution, and dried and concentrated under reduced pressure. It was then recrystallized with hexane and ethyl acetate to obtain a white solid (0.62 g, 91%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 1 hour
  3. extractionit was extracted with ethyl acetate
  4. distillationAfter distillation under reduced pressure and vacuum
  5. customdrying
  6. dissolutionthe mixture was dissolved in 20 mL of dichloromethane
  7. temperaturewhile maintaining the temperature at 0° C
  8. customAfter reaction for 6 hours
  9. washthe reactant was washed with a saturated NaHCO3 aqueous solution
  10. dry with materiala 1N HCl aqueous solution, and dried
  11. concentrationconcentrated under reduced pressure
  12. customIt was then recrystallized with hexane and ethyl acetate

Sources & evidence

ORD record
ord-b185b26efe3e42a68fd14e8d745d0d63
Source dataset
uspto-grants-2007_05
Patent number
US07223751B2

Reaction notes

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