Ethylamine → HCID 9928906, compound

HRID 2255505Notes

Reaction equation

HRID 2255505 reaction equation
O[CH:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[S:5](=[O:16])(=[O:15])[N:4]([CH3:17])[CH2:3]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:29]([N:31](CC)CC)[CH3:30].C(N)C.S(C1C=CC(C)=CC=1)([O-])(=O)=O>O1CCCC1>[CH2:29]([NH:31][CH:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[S:5](=[O:16])(=[O:15])[N:4]([CH3:17])[CH2:3]1)[CH3:30]

Participants

7

Reactant 5

HCID 6341EthylamineHCID 73974-Toluenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 85570p-ToluenesulfonateHCID 19737936HCID 19737936, compound

Product 1

HCID 9928906HCID 9928906, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, a stirred solution of the compound from Step E (5.00 g, 16.8 mmol) and p-toluenesulfonyl chloride (1.1 eq, 18.5 mmol, 3.30 g) in tetrahydrofuran (100 mL) was treated with triethylamine (1.1 eq, 2.78 mL). After 18 h at room temperature, TLC. indicated that starting material was still present so additional p-toluenesulfonyl chloride (0.4 eq, 1.3 g) and triethylamine (0.4 eq, 1.0 mL) was added. Stirring was continued for another 18 h, at which point TLC. indicated the absence of starting material. Ethylamine (18 g) was added to the reaction mixture and the flask was stoppered. After 18 h at room temperature, TLC. indicated that the intermediate tosylate was absent. At this point, the reaction mixture was combined with another 1.55 g run for workup. The mixture was partitioned between 1 M aqueous hydrochloric acid (100 mL) and diethyl ether (250 mL) and the acidic aqueous phase was separated. The organic phase was further extracted with 1 M aqueous hydrochloric acid (3×100 mL), and the combined aqueous layers were then back washed with ether (3×100 mL), basified using solid sodium bicarbonate, and extracted with ethyl acetate (4×250 mL). The combined organic ethyl acetate extracts were dried over MgSO4, treated with decolorizing carbon (Norite A), filtered through celite, and concentrated under reduced pressure, to provide 5.2 g (73%) of the sulfonamide.

Workup

  1. additionwas added
  2. waitwas continued for another 18 h, at which point TLC
  3. waitAfter 18 h at room temperature
  4. customThe mixture was partitioned between 1 M aqueous hydrochloric acid (100 mL) and diethyl ether (250 mL)
  5. customthe acidic aqueous phase was separated
  6. extractionThe organic phase was further extracted with 1 M aqueous hydrochloric acid (3×100 mL)
  7. washthe combined aqueous layers were then back washed with ether (3×100 mL)
  8. extractionextracted with ethyl acetate (4×250 mL)
  9. dry with materialThe combined organic ethyl acetate extracts were dried over MgSO4
  10. additiontreated with decolorizing carbon (Norite A),
  11. filtrationfiltered through celite
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-014f367a1b394f5f87a4f0d4ff9be5a2
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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