Benzenesulfonyl chloride, 4-chloro-3-nitro- → HCID 5323285, compound

HRID 1709795Notes

Reaction equation

HRID 1709795 reaction equation
[OH-].[Na+].[CH2:3]([NH:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:5][CH3:6].[N+:12]([C:15]1[CH:16]=[C:17]([S:22](Cl)(=[O:24])=[O:23])[CH:18]=[CH:19][C:20]=1[Cl:21])([O-:14])=[O:13]>O.C(#N)C>[CH2:3]([N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[S:22]([C:17]1[CH:18]=[CH:19][C:20]([Cl:21])=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=1)(=[O:23])=[O:24])[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8148DibutylamineHCID 14798Sodium Hydroxide

Product 1

HCID 5323285HCID 5323285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

150 g of sodium hydroxide was dissolved in 200 ml of water, and the solution was cooled. To this solution was added 600 ml of dibutylamine, and the solution was cooled to 0° C. A solution of 954 g of 3-nitro-4-chlorobenzenesulfonyl chloride in 950 ml of acetonitrile was dropwise added thereto under vigorous stirring while keeping the solution temperature at not higher than 10° C. After completion of the dropwise addition, the reaction mixture was stirred for 1 hour at 10° C., and the crystals which precipitated were collected by filtration, washed wellwith a dilute hydrochloric acid aqueous solution (1N), and dried.

Workup

  1. temperaturethe solution was cooled
  2. customhigher than 10° C
  3. additionAfter completion of the dropwise addition
  4. stirringthe reaction mixture was stirred for 1 hour at 10° C.
  5. customthe crystals which precipitated
  6. filtrationwere collected by filtration
  7. washwashed wellwith a dilute hydrochloric acid aqueous solution (1N)
  8. customdried

Sources & evidence

ORD record
ord-696ab2416f04418f8befb6853bccb28d
Source dataset
uspto-grants-1990_08
Patent number
US04950764

Reaction notes

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