4-Toluenesulfonyl chloride → HCID 3090868, compound

HRID 2259545Notes

Reaction equation

HRID 2259545 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N([CH2:17][CH3:18])CC)C.[CH2:19]([N:26]([CH2:30][CH2:31][NH2:32])[CH2:27][CH2:28][NH2:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.C(OCC)(=O)C.CCOCC>[CH2:19]([N:26]([CH2:30][CH2:31][NH:32][S:7]([C:4]1[CH:5]=[CH:6][C:17]([CH3:18])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:27][CH2:28][NH:29][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10081318N'-(2-aminoethyl)-N'-benzylethane-1,2-diamine

Product 1

HCID 3090868HCID 3090868, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 141.2 g (0.741 mol) of p-toluenesulfonyl chloride in 250 ml of dichloromethane with 110 ml (0.8 mol) of triethylamine was added dropwise 68.0 g (0.352 mol) of 4-benzyl-1,4,7-triazaheptane in 75 ml of dichloromethane. After 2 hours, the solution was washed three times with water at pH 9, and the organic phase was dried with sodium sulfate and filtered. Evaporation gave an oil which was dissolved in about 450 ml of ethyl acetate. The solution was diluted with 200 ml of ether and left to stand at room temperature for 24 hours. The mixture was further diluted with about 50 ml of ether and refrigerated for another day. The product crystallized in massive prisms which were collected by filtration and dried under vacuum at 40° C. for 6 hours, yielding in the first crop 140 g (0.279 mol) of a colorless solid; melting point 87°-91° C. Mass spectrum (CI): m/e 502 (M+H) and 500 (M-H).

Workup

  1. washthe solution was washed three times with water at pH 9
  2. dry with materialthe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. customEvaporation
  5. customgave an oil which
  6. waitleft
  7. waitto stand at room temperature for 24 hours
  8. waitrefrigerated for another day
  9. customThe product crystallized in massive prisms which
  10. filtrationwere collected by filtration
  11. customdried under vacuum at 40° C. for 6 hours

Sources & evidence

ORD record
ord-e5cc38333f1b4b238751de3a70c7d443
Source dataset
uspto-grants-1995_12
Patent number
US05474756

Reaction notes

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