Mechlorethamine → HCID 18705611, compound

HRID 2287800Notes

Reaction equation

HRID 2287800 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+].[CH3:53][N:54]([CH2:58][CH2:59]Cl)[CH2:55][CH2:56]Cl>CN(C=O)C>[CH3:53][N:54]1[CH2:58][CH2:59][N:19]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:18][CH2:17][N:16]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:31])=[O:32])[CH2:15][CH2:14][N:13]([S:40]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)(=[O:41])=[O:42])[CH2:12][CH2:11][N:10]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:50])=[CH:2][CH:3]=2)(=[O:8])=[O:9])[CH2:56][CH2:55]1

Participants

5

Reactant 3

HCID 4033MechlorethamineHCID 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 18705611HCID 18705611, compoundYield 85%

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 (66.5 g, 0.0872 mole) in anhydrous DMF (1 l) was added sodium hydride (5.22 g--80% in mineral oil, 0.174 mole) in portions under a dry nitrogen blanket. 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 N-methylbis(2-chloroethyl)amine freshly prepared as in Example 15A (13.6 g, 0.0872 mole) in anhydrous DMF (200 ml) was added dropwise over a 1.5 h period, maintaining the temperature at 100° C. After stirring an additional 45 minutes at 100° C., the solution was concentrated in vacuo to a volume of 750 ml. H2O was slowly added at room temperature to crystallize the product. The resulting brown solid was filtered, washed thoroughly with H2O and dried in vacuo over P2O, to give 62.9 g (85% yield) of the crude product as a brown solid. The product was purified by crystallization from DMF-H2O to give a yellow solid: mp 170-1° C.; 1H NMR (CDCl3) δ 2.15 (s, 3 H), 2.43 (s, 6 H), 2.44 (s, 6 H), 2.51 (t, J=5.5 Hz, 4 H), 3.15 (t, J=5.5 Hz, 4 H), 3.29 (m, 8 H), 3.36 (s, 4 H), 7.32 (m, 8 H), 7.69 (m, 8 H).

Workup

  1. additionwas added dropwise over a 1.5 h period
  2. temperaturemaintaining the temperature at 100° C
  3. stirringAfter stirring an additional 45 minutes at 100° C.
  4. concentrationthe solution was concentrated in vacuo to a volume of 750 ml
  5. additionH2O was slowly added at room temperature
  6. customto crystallize the product
  7. filtrationThe resulting brown solid was filtered
  8. washwashed thoroughly with H2O
  9. customdried in vacuo over P2O

Sources & evidence

ORD record
ord-ec9f99a978234dce811b1918022ddc39
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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