Triethylamine → HCID 14404109, compound

HRID 465503Notes

Reaction equation

HRID 465503 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][N+:12]([O-:14])=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25]>O1CCCC1>[C:22]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][N+:12]([O-:14])=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1)(=[O:26])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 10680224HCID 10680224, compound

Product 1

HCID 14404109HCID 14404109, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Aminophenylsulphonyl)nitromethane (1.62 g, 7.5 mmol) was dissolved in dry tetrahydrofuran (35 ml) under an atmosphere of argon. Triethylamine (1.14 g, 11.25 mmol) was added, followed by butyryl chloride (0.88 g, 8.25 mmol). The mixture was stirred for 2 hours. The precipitated triethylamine hydrochloride was removed by filtration and the filtrate concentrated in vacuo. The brown oil obtained was purified by MPLC, eluting with dichloromethane/methanol (99:1 v/v) to give (4-butyramidophenylsulphonyl)nitromethane (0.16 g, 7.5% yield) as a solid, m.p. 155 156° C.; microanalysis, found: C, 45.8; H, 4.8; N, 9.6%; C11H14N2O5S requires: C, 46.1; H, 4.9; N, 9.8%.

Workup

  1. customThe precipitated triethylamine hydrochloride was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe brown oil obtained
  4. customwas purified by MPLC
  5. washeluting with dichloromethane/methanol (99:1 v/v)

Sources & evidence

ORD record
ord-24404ca36e114de9a5a6fe56b951eddc
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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