Hydrochloric Acid → HCID 19805552, compound

HRID 2248130Notes

Reaction equation

HRID 2248130 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.Cl>C(Cl)Cl>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:10][CH2:9][CH2:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 951534-Nitrophenethylamine

Product 1

HCID 19805552HCID 19805552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

14.1 g. (85 mMol) of the above-obtained p-nitrophenethylamine and 34 ml. (340 mMol) triethylamine are dissolved in 170 ml. methylene chloride and 17.9 g. (85 mMol) p-chlorobenzenesulphonic acid chloride in 170 ml. methylene chloride added dropwise thereto at 0° to 5° C. within the course of 1 hour. After stirring for a further hour at 0° C., the reaction mixture is allowed to warm up to ambient temperature. It is then poured on to ice, mixed with 2N hydrochloric acid and shaken out with methylene chloride. The organic phase is washed neutral, dried over anhydrous magnesium sulphate and evaporated to dryness. The oily residue is chromatographed over silica gel with ligroin/ethyl acetate/glacial acetic acid (1.5:1.0:0.006 v/v/v) as elution agent. There are obtained 10.2 g. (35% of theory) of the desired compound in the form of a colourless oil. 1H-NMR (60 MHz, d6 -DMSO, ppm): δ=2.7-3.1 (m, 5H, CH2, NH); 7.35 and 8.10 (AB system 2d, J=9.5 Hz, 4H); 7.55 and 7.75 (AB system, 2d, J=10 Hz, 4H).

Workup

  1. customat 0° to 5° C.
  2. customwithin the course of 1 hour
  3. temperatureto warm up to ambient temperature
  4. additionIt is then poured on to ice
  5. washThe organic phase is washed neutral
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated to dryness
  8. customThe oily residue is chromatographed over silica gel with ligroin/ethyl acetate/glacial acetic acid (1.5:1.0:0.006 v/v/v) as elution agent
  9. customThere are obtained 10.2 g

Sources & evidence

ORD record
ord-b5fa2a3914524f55be90d8610475cb7f
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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