Benzenesulfonyl chloride → HCID 118006539, compound

HRID 1486794Notes

Reaction equation

HRID 1486794 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][CH2:8][CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(OC)(C)C>O.C(Cl)Cl>[CH2:12]([O:11][CH:10]([O:14][CH2:15][CH3:16])[CH2:9][CH2:8][NH:7][S:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:25])=[O:24])[CH3:13]

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 15413tert-Butyl methyl etherHCID 5210291-Amino-3,3-diethoxypropane

Product 1

HCID 118006539HCID 118006539, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of sodium carbonate (31 g, 0.37 mol) in water (50 ml) was added a solution of 1-amino-3,3-diethoxypropane (10.00 mL, 61.81 mmol) in DCM (50 mL) followed by cooling to 0° C. benzenesulfonyl chloride (7.65 mL, 60.0 mmol) was added at 0° C. with vigorous stirring followed by warming to 20° C. and continued stirring for 2 h after which time MTBE (150 mL) was added. Organic layer was separated, washed with 1.0 M of HCl (50 mL), saturated NaHCO3 (50 g), water (50 g), concentrated and azeotroped to dry two times with MTBE (150 mL×2) to provide N-(3,3-diethoxypropyl)benzenesulfonamide, 28 (17.34 g, 60.34 mmol, 97% yield) as light yellow clear oil.

Workup

  1. additionwas added at 0° C.
  2. additionwas added
  3. customOrganic layer was separated
  4. washwashed with 1.0 M of HCl (50 mL), saturated NaHCO3 (50 g), water (50 g)
  5. concentrationconcentrated
  6. customazeotroped
  7. dry with materialto dry two times with MTBE (150 mL×2)

Sources & evidence

ORD record
ord-044659ce79e24ad289fe83c2e257a7ab
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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