Hydrochloric Acid → 2-Chloro-N,N-diethyl-5-nitrobenzene-1-sulfonamide

HRID 1709958Notes

Reaction equation

HRID 1709958 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[CH2:15]([N:17](CC)[CH2:18][CH3:19])[CH3:16].C(NCC)C.Cl>CC(C)=O.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](=[O:13])(=[O:12])[N:17]([CH2:18][CH3:19])[CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 8471TriethylamineHCID 206302-Chloro-5-nitrobenzenesulfonyl chloride

Product 1

HCID 50194162-Chloro-N,N-diethyl-5-nitrobenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

7.6 g of 2-chloro-5-nitrophenylsulfonyl chloride was dissolved in 50 g of acetone, and the obtained solution was then cooled to -10° C. A solution obtained by dissolving 3.03 g of triethylamine and 2.2 g of diethylamine in 20 g of acetonitrile was added dropwisely to the obtained solution. During the addition, the mixture was agitated under cooling so that the temperature did not exceed 0° C. The temperature was gradually raised to room temperature, and the mixture was poured into a dilute solution of hydrochloric acid at pH of about 2. The produced crystals were filtered off and washed with water (yield: 7.8 g).

Workup

  1. customA solution obtained
  2. additionwas added dropwisely to the obtained solution
  3. additionDuring the addition
  4. temperatureunder cooling so that the temperature
  5. customdid not exceed 0° C
  6. temperatureThe temperature was gradually raised to room temperature
  7. filtrationThe produced crystals were filtered off
  8. washwashed with water (yield: 7.8 g)

Sources & evidence

ORD record
ord-4d7de9714c8544629ddc86fd7f70c89f
Source dataset
uspto-grants-1990_08
Patent number
US04952483

Reaction notes

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