Hydrochloric Acid → 4-methyl-N-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonylamino]ethyl]amino]ethyl]amino]ethyl]benzenesulfonamide

HRID 1414444Notes

Reaction equation

HRID 1414444 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][NH2:21].Cl>N1C=CC=CC=1>[S:8]([NH:12][CH2:13][CH2:14][N:15]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH2:16][CH2:17][N:18]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH2:19][CH2:20][NH:21][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5565TriethylenetetramineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 3166814-methyl-N-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonylamino]ethyl]amino]ethyl]amino]ethyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Procedure 3 is further illustrated by the preparation of racemic 6e'. A solution of 80 g of p-tosyl chloride in 300 ml. of dry pyridine was cooled to 0° and added to a cooled, stirred solution of triethylenetetramine (MCB, technical) in 50 ml. of dry pyridine over a period of 3 hr. The solution was kept at 0° during addition. The solution was allowed to stand at 0° for 24 hrs, and mixed with 100 ml. of concentrated hydrochloric acid and 1 kg. of crushed ice. The resulting aqueous solution was decanted, and the oily residue was triturated with methanol, filtered, and recrystallized twice from 50 ml. of dimethyl formamide and 300 ml. of 95% ethanol to give N,N',N",N'"-tetratosyltriethylenetetramine, 28.8 g. (38%), m.p. 211°-213°. The analytical sample was dried at 180° for 14 hrs at 10μ.

Workup

  1. additionadded to a cooled
  2. additionThe solution was kept at 0° during addition
  3. additionmixed with 100 ml
  4. customThe resulting aqueous solution was decanted
  5. customthe oily residue was triturated with methanol
  6. filtrationfiltered
  7. customrecrystallized twice from 50 ml

Sources & evidence

ORD record
ord-9fd933a6738e4fbf980a1bf63a04bce4
Source dataset
uspto-grants-1977_01
Patent number
US04001279

Reaction notes

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