4-Nitrobenzenesulfonyl chloride → HCID 874568, compound

HRID 624231Notes

Reaction equation

HRID 624231 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[CH3:23][CH:24]([CH3:28])[CH2:25][CH2:26][NH2:27]>ClCCl.C(=O)(O)[O-].[Na+]>[CH2:26]([NH:27][S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11])[CH2:25][CH:24]([CH3:28])[CH3:23]

Participants

6

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 7894IsoamylamineHCID 81531Diisopropylethylamine

Product 1

HCID 874568HCID 874568, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitrobenzene-1-sulfonyl chloride (1.5 g, 6.57 mmol) was dissolved in dichloromethane (30 ml) and cooled to 0° C. followed by addition of diisopropylethylamine (2.293 ml, 13.13 mmol). 3-Methylbutan-1-amine (0.926 ml, 7.88 mmol) was dissolved in 5 ml dichloromethane and added via syringe. After the addition, the mixture was allowed to warm to room temperature for 3 hours. The solution was diluted with aqueous sodium bicarbonate and extracted twice with dichloromethane. The organics were combined, dried over magnesium sulfate, filtered and concentrated. Chromatography provided the title compound.

Workup

  1. additionadded via syringe
  2. additionAfter the addition
  3. temperatureto warm to room temperature for 3 hours
  4. extractionextracted twice with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d0c461296de4417fb3d1e87938df67cf
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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