Benzoyl chloride → HCID 14404099, compound

HRID 465500Notes

Reaction equation

HRID 465500 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:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>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:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10680224HCID 10680224, compound

Product 1

HCID 14404099HCID 14404099, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Aminophenylsulphonyl)nitromethane (0.86 g, 4 mmol) was dissolved in dry tetrahydrofuran (20 ml) under an atmosphere of argon. Triethylamine (0.61 g, 6 mmol) was added, followed by benzoyl chloride (0.62 g, 4.4 mmol). The mixture was then stirred for 2 hours. The precipitated triethylamine hydrochloride was removed by filtration and the filtrate concentrated in vacuo. The orange oil obtained was purified by MPLC, eluting with dichloromethane/ethyl acetate (9:1 v/v) to give (4-benzamidophenylsulphonyl)nitromethane (0.25 g, 20% yield) as a solid, m.p. 211°-212° C.; microanalysis, found: C, 52.3; H, 3.7; N, 8.4%; C14H12N2O5S requires: C, 52.5; H, 3.75; N, 8.75%.

Workup

  1. customThe precipitated triethylamine hydrochloride was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe orange oil obtained
  4. customwas purified by MPLC
  5. washeluting with dichloromethane/ethyl acetate (9:1 v/v)

Sources & evidence

ORD record
ord-7bb7677f318b4b5791a1ae7d13dbc7dc
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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