Triethylamine → HCID 66863768, compound

HRID 45982Notes

Reaction equation

HRID 45982 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:15]([N:18]([CH2:23][CH:24]=[CH2:25])[S:19]([NH2:22])(=[O:21])=[O:20])[CH2:16][CH3:17].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([NH:22][S:19]([N:18]([CH2:23][CH2:24][CH3:25])[CH2:15][CH:16]=[CH2:17])(=[O:21])=[O:20])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chlorideHCID 85888395HCID 85888395, compound

Product 1

HCID 66863768HCID 66863768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At from −5° C. to 0° C., 11.62 g (0.0474 mol) of 2-chloro-4-fluoro-5-nitrobenzoyl chloride in 50 ml methylene chloride were added with stirring, over 30 minutes, to a mixture of 8.50 g (0.048 mol) of N′-propyl-N′-allylsulfamide, 10.38 g (0.103 mol) of triethylamine and 0.09 g (0.736 mmol) of 4-N,N-dimethylaminopyridine in 90 ml of methylene chloride. The funnel was rinsed with 10 ml of the solvent. The mixture was initially stirred at 0° C. for 1 hour and then at 22° C. for 2 hours. 50 ml of 1N hydrochloric acid were then added, the mixture was stirred and the phases were separated. The organic phase was washed two more times with 1N hydrochloric acid and the aqueous phase was extracted with methylene chloride. Drying of the organic phase over magnesium sulfate was followed by filtration and concentration of the solution. The residue was triturated with diethyl ether/pentane, filtered off with suction and dried, giving 18.41 g (91.9% of theory) of the title compound of melting point (m.p.) of 110-112° C.

Workup

  1. washThe funnel was rinsed with 10 ml of the solvent
  2. waitat 22° C. for 2 hours
  3. addition50 ml of 1N hydrochloric acid were then added
  4. stirringthe mixture was stirred
  5. customthe phases were separated
  6. washThe organic phase was washed two more times with 1N hydrochloric acid
  7. extractionthe aqueous phase was extracted with methylene chloride
  8. dry with materialDrying of the organic phase over magnesium sulfate
  9. filtrationwas followed by filtration and concentration of the solution
  10. customThe residue was triturated with diethyl ether/pentane
  11. filtrationfiltered off with suction
  12. customdried

Sources & evidence

ORD record
ord-c92fdd6f12d54f4ab4f63cadf48129ee
Source dataset
uspto-grants-2013_09
Patent number
US08541611B2

Reaction notes

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