Triethylamine → 1-[4-[(Methylsulfonyl)amino]benzoyl]aziridine

HRID 1199494Notes

Reaction equation

HRID 1199494 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[NH:15]1[CH2:17][CH2:16]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([N:15]2[CH2:17][CH2:16]2)=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9033AziridineHCID 117911194-[(Methylsulfonyl)amino]benzoyl chloride

Product 1

HCID 147735491-[4-[(Methylsulfonyl)amino]benzoyl]aziridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

13.0 g (55.6 mmol) of 4-[(methylsulfonyl)amino]benzoyl chloride is suspended in 150 mL of methylene chloride and cooled to about 0° C. 2.40 g (55.7 mmol) of aziridine and 7.75 mL (55.6 mmol) of triethylamine are added and the reaction allowed to warm to room temperature and stir for 2 hours. After 2 hours, the solution is washed with 100 mL of saturated aqueous sodium chloride and placed in the freezer. After 18 hours, the resulting white precipitate is filtered, washed with 50 mL of ether and dried to provide the title compound.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 2 hours
  3. washthe solution is washed with 100 mL of saturated aqueous sodium chloride
  4. waitAfter 18 hours
  5. filtrationthe resulting white precipitate is filtered
  6. washwashed with 50 mL of ether
  7. customdried

Sources & evidence

ORD record
ord-cab3e4b782604ee880c0f55346d0d0a3
Source dataset
uspto-grants-1990_02
Patent number
US04900841

Reaction notes

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