Triethylamine → HCID 58496687, compound

HRID 1697274Notes

Reaction equation

HRID 1697274 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:14][C:15]1[CH:16]=[C:17]([S:22]([NH:25][C:26]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:27]=2[CH:28]=[CH:29][CH:30]=[C:31]3[C:36]([NH2:38])=O)(=[O:24])=[O:23])[CH:18]=[C:19]([Cl:21])[CH:20]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:21][C:19]1[CH:18]=[C:17]([S:22]([NH:25][C:26]2[C:27]3[C:32](=[C:31]([C:36]#[N:38])[CH:30]=[CH:29][CH:28]=3)[CH:33]=[CH:34][CH:35]=2)(=[O:24])=[O:23])[CH:16]=[C:15]([Cl:14])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 58496694HCID 58496694, compound

Product 1

HCID 58496687HCID 58496687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.49 ml trifluoroacetic anhydride are added dropwise to a mixture of 1.13 g 5-(3,5-dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid amide and 1.07 ml triethylamine in 50 ml methylene chloride while cooling with an ice bath. Then the ice bath is removed and the reaction mixture is stirred for one hour at ambient temperature. In all, another 1.00 ml triethylamine and 0.70 ml trifluoroacetic anhydride are added successively and the reaction mixture is stirred overnight at ambient temperature. For working up the mixture is combined with 50 ml of water. The organic phase is washed with 2 N citric acid solution and saturated sodium hydrogen carbonate solution, dried on magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (85:15 to 65:35).

Workup

  1. temperaturewhile cooling with an ice bath
  2. customThen the ice bath is removed
  3. additionIn all, another 1.00 ml triethylamine and 0.70 ml trifluoroacetic anhydride are added successively
  4. stirringthe reaction mixture is stirred overnight at ambient temperature
  5. washThe organic phase is washed with 2 N citric acid solution and saturated sodium hydrogen carbonate solution
  6. customdried on magnesium sulphate
  7. customevaporated down
  8. customThe flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (85:15 to 65:35)

Sources & evidence

ORD record
ord-ac8afecf552c4dd9a2216946560c2b20
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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