Water → N-ethyl-2-nitrobenzenesulfonamide

HRID 1615028Notes

Reaction equation

HRID 1615028 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH2:14]([NH2:16])[CH3:15].C([O-])([O-])=O.[Na+].[Na+].O>C(OCC)(=O)C.C(Cl)Cl>[CH2:14]([NH:16][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 10340Sodium CarbonateHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 744706N-ethyl-2-nitrobenzenesulfonamideYield 161.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-nitrobenzenesulfonyl chloride (140 g, 361 mmol) in ethyl acetate (250 mL) was added dropwise at room temperature to a mixture of 70% aqueous ethylamine (50 mL, 630 mmol), ethyl acetate (100 mL), Na2CO3 (67 g, 632 mmol), and water (250 mL). The reaction mixture was stirred for 4 h (TLC monitoring, CH2Cl2). The organic layer was separated, washed with water, with a solution of citric acid, dried with Na2SO4, and evaporated. The residue solidified into a white crystalline mass. The latter was triturated with hexane, filtered off, and dried to give 134 g (92%) of the product.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, with a solution of citric acid
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe latter was triturated with hexane
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-f4b9bdf6c3c7402385855f10598456d3
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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