Water → HCID 10930869, compound

HRID 2287804Notes

Reaction equation

HRID 2287804 reaction equation
[C:1]1([CH3:50])[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH2:11][CH2:12][N:13]([S:40]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)(=[O:42])=[O:41])[CH2:14][CH2:15][N:16]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:54][CH2:55][O:56][CH2:57][CH2:58]Cl.O>CN(C=O)C>[C:26]1([CH3:29])[CH:27]=[CH:28][C:23]([S:20]([N:19]2[CH2:18][CH2:17][N:16]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:31])=[O:32])[CH2:15][CH2:14][N:13]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:41])=[O:42])[CH2:12][CH2:11][N:10]([S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:50])=[CH:2][CH:3]=3)(=[O:8])=[O:9])[CH2:58][CH2:57][O:56][CH2:55][CH2:54]2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 3166814-methyl-N-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonyl-[2-[(4-methylphenyl)sulfonylamino]ethyl]amino]ethyl]amino]ethyl]benzenesulfonamide

Product 1

HCID 10930869HCID 10930869, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 1,4,7,10-tetra(p-toluenesulfonyl)-1,4,7,10-tetraazadecane prepared as in Example 15B (35.3 g, 0.0463 mole) in anhydrous DMF (460 ml) was added sodium hydride (2.77 g--80% in mineral oil, 0.0925 mole) in portions and the resulting mixture was stirred for 30 minutes under a dry argon atmosphere. The solution was then heated to 100° C. and a solution of 2-chloroethyl ether (6.61 g, 0.0463 mole) in anhydrous DMF (90 ml) was added dropwise over a 1.5 h period, maintaining the temperature at 100° C. After stirring the solution an additional 1.5 h at 100° C., H2O (3 l) was added while cooling (ice bath) to crystallize the product. The resulting tan solid was filtered and dried in vacuo. The crude product was purified by crystallization from CH2Cl2 -hexane to give 13.2 g (34% yield) of the product as an off-white solid: mp 197.5-201° C.; 1H NMR (CDCl3) δ 2.44 (s, 12 H), 3.28 (m, 16 H), 3.57 (m, 4 H), 7.35 (m, 8 H), 7.69 (m, 8 H).

Workup

  1. temperaturemaintaining the temperature at 100° C
  2. stirringAfter stirring the solution an additional 1.5 h at 100° C.
  3. temperaturewhile cooling (ice bath)
  4. customto crystallize the product
  5. filtrationThe resulting tan solid was filtered
  6. customdried in vacuo
  7. customThe crude product was purified by crystallization from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-08e324d9648a4cd0ba8e6eba062bb73f
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

Loading…