Mechlorethamine → HCID 68594997, compound

HRID 1800818Notes

Reaction equation

HRID 1800818 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:14][CH2:15][N:16]([CH2:18][CH2:19]Cl)[CH3:17]>CS(C)=O.Cl>[CH3:17][N:16]1[CH2:18][CH2:19][C:8]([C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)([C:9]#[N:10])[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 4033MechlorethamineHCID 24758Sodium hydrideHCID 123966084-Pyridylacetonitrile hydrochloride

Product 1

HCID 68594997HCID 68594997, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 4-pyridyl acetonitrile hydrochloride (1.0 g, 6.47 mmol) in DMSO (8 mL) was treated with sodium hydride (0.735 g, 29.11 mmol) portionwise. The resulting suspension was stirred at 23° C. for 30 minutes. 2-Chloro-N-(2-chloroethyl)-N-methylethanamine (1.37 g, 7.11 mmol) was then slowly added over 5 minutes, then the suspension was heated at 65° C. overnight. The reaction was then diluted with 1N hydrochloric acid and washed with ethyl acetate (2×). The aqueous phase was basified with 5N sodium hydroxide and extracted with ethyl acetate (3×). The combined extracts were washed with water (5×), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil (0.200 g, 15%) which was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 2.10-2.17 (3H, m), 2.31-2.37 (1H, m), 2.42 (3H, s), 2.47-2.57 (2H, m), 3.01 (2G, d, J=12.6 Hz), 7.45 (2H, dd, J=4.55 and 1.52 Hz), 8.68 (2H, dd, J=4.55 and 1.77 Hz).

Workup

  1. temperaturethe suspension was heated at 65° C. overnight
  2. washwashed with ethyl acetate (2×)
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined extracts were washed with water (5×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d7a3c33d26334db9a165a3d426ee87b3
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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