4-Toluenesulfonyl chloride → HCID 86751730, compound

HRID 1939875Notes

Reaction equation

HRID 1939875 reaction equation
[C:1]12[CH:22]=[CH:21][CH:20]=[C:19]([N:23]=1)[CH2:18][NH:17][CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[N:24][C:8](=[CH:9][CH:10]=[CH:11]1)[CH2:7][NH:6][CH2:5][CH2:4][NH:3][CH2:2]2.C(N([CH2:30][CH3:31])CC)C.ClCl.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>>[C:30]1([CH3:31])[CH:39]=[CH:38][C:37]([S:40]([N:17]2[CH2:16][CH2:15][N:14]([S:40]([C:37]3[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=3)(=[O:42])=[O:41])[CH2:13][C:12]3[N:24]=[C:8]([CH:9]=[CH:10][CH:11]=3)[CH2:7][N:6]([S:40]([C:37]3[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=3)(=[O:42])=[O:41])[CH2:5][CH2:4][NH:3][CH2:2][C:1]3[N:23]=[C:19]([CH:20]=[CH:21][CH:22]=3)[CH2:18]2)(=[O:42])=[O:41])=[CH:36][CH:35]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 24526Chlorine2×HCID 12092972HCID 12092972, compound

Product 1

HCID 86751730HCID 86751730, compoundYield 27%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3,6,14,17,23,24-hexaazatricyclo-[17.3.1.18,12 ]tetracosa-1(23),8,10,12(24),19,21-hexaene (460 mg, 1.41 mmol) (G L Rothermel, L Miao, A L Hill, L C Jackels, Inorg Chem, 1992, 31, 4854) and triethylamine (0.60 ml, 4.233 mmol) at 0° C. in 40 ml of CH2 Cl2 under an argon atmosphere was added a solution of p-toluenesulphonyl chloride (804 mg, 4.233 mmol) in 10 ml of CH2 Cl2 dropwise over 15 min. The solution was stirred at 0° C. for 30 minutes and warmed to room temperature and stirred a further 4 hours. The reaction mixture was quenched with saturated NH4Cl (10 ml), the aqueous phase extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 5% MeOH in CH2Cl2 as eluent giving 3,6,14-tris(p-toluenesulphonyl)-3,6,14,17,23,24-hexaaza-tricyclo[17.3.1.18,12 ]tetracosa-1(23),8,10,12(24),19,21-hexaene (300 mg, 27%) as a white solid.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred a further 4 hours
  3. customThe reaction mixture was quenched with saturated NH4Cl (10 ml)
  4. extractionthe aqueous phase extracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel using 5% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-93df06ae111c4e52bda9229d7593a0a0
Source dataset
uspto-grants-1997_12
Patent number
US05698546

Reaction notes

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