Triethylamine → HCID 21745509, compound

HRID 2379334Notes

Reaction equation

HRID 2379334 reaction equation
[F:1][C:2]([S:5]([NH2:8])(=[O:7])=[O:6])([F:4])[F:3].C(N(CC)CC)C.[N+:16]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23])([O-:18])=[O:17]>ClCCl>[F:1][C:2]([F:4])([F:3])[S:5]([NH:8][C:22]([C:21]1[CH:25]=[CH:26][CH:27]=[C:19]([N+:16]([O-:18])=[O:17])[CH:20]=1)=[O:23])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 79001Trifluoromethylsulfonamide

Product 1

HCID 21745509HCID 21745509, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifiuoromethylsulphonamide (2.1 g, 14.1 mmol) in anhydrous dichloromethane (50 ml), cooled to 0° C. was treated with triethylamine (2.0 ml, 14.1 mmol) followed by a solution of 3-nitrobenzoyl chloride (2.5 g, 13.4 mmol) in anhydrous dichloromethane (50ml) dropwise. After stirring at 0° C. for 1h, the mixture was stirred at ambient temperature for 2 h. The mixture was extracted using 1M NaOH (100 ml), and the aqueous phase was acidified using 5M HCl. The aqueous phase was then extracted using dichloromethane (4×100 ml), followed by ethyl acetate (2×100 ml). The combined organic layers were dried (Na2SO4) and evaporated in vacuo to leave a yellow solid. This was recrystallised from diethyl ether:hexane (1:1) to afford the title compound (1.5 g, 36%) as a pale yellow solid. mp 80°-83° C. 1H NMR (360 MHz, D6 -DMSO) δ 7.73 (1H, dd, J=8.0 and 8.0 Hz), 8.35 (2H, m), 8.56 (1H, brs), 8.68 (1H, m).

Workup

  1. extractionThe mixture was extracted
  2. extractionThe aqueous phase was then extracted
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto leave a yellow solid
  6. customThis was recrystallised from diethyl ether:hexane (1:1)

Sources & evidence

ORD record
ord-5f19cb93528242bf97a79f50bc97d404
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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