4-Chloro-3-nitrobenzenesulfonamide → HCID 22660807, compound

HRID 392988Notes

Reaction equation

HRID 392988 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>C(#N)C>[CH:15]1([NH:21][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 7965CyclohexylamineHCID 8471Triethylamine

Product 1

HCID 22660807HCID 22660807, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-chloro-3-nitro-benzene sulfonamide (5.49 g, 23.2 mmol), cyclohexylamine (4.00 mL, 35.0 mmol), and triethylamine (5.0 mL, 35 mmol) in acetonitrile (75 mL) was refluxed overnight under nitrogen atmosphere. The reaction mixture was concentrated almost to dryness. The residue was diluted in ethyl acetate and washed with 1N hydrochloric acid (1×) and saturated NaHCO3 (1×). The organic layer was dried (MgSO4) and concentrated on a rotary evaporator. The residue was filtered and washed with hexane to give the product as a yellow solid (6.34 g, 91%). ESI-MS m/e 300.1 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated almost to dryness
  2. additionThe residue was diluted in ethyl acetate
  3. washwashed with 1N hydrochloric acid (1×) and saturated NaHCO3 (1×)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated on a rotary evaporator
  6. filtrationThe residue was filtered
  7. washwashed with hexane

Sources & evidence

ORD record
ord-5bd9cdf0e1f144139a452e9d647772cc
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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