Ethanol → Pentamustine

HRID 905257Notes

Reaction equation

HRID 905257 reaction equation
[CH2:1]([NH:6][C:7]([NH:9][CH2:10][CH2:11][Cl:12])=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3].C(O)C.[N:16]([O-])=[O:17].[Na+]>Cl.O>[CH2:1]([NH:6][C:7]([N:9]([CH2:10][CH2:11][Cl:12])[N:16]=[O:17])=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 13254209HCID 13254209, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 3037028Pentamustine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The entire yield of 1-neopentyl-3-(2-chloroethyl) urea (0.08 mol) was dissolved in 120 ml of concentrated HCl:ethanol, 2:1 at 5° C. in a 500 ml round bottom flask equipped with magnetic stirring. Sodium nitrite (5.5 g, 0.08 mol) was dissolved in 30 ml of water and added to the solution over a ten-minute period. Stirring continued for 2 hrs, and the yellow, crystalline precipitate was filtered and washed with five 100 ml portions of chilled distilled water. The product was dried in vacuo for 18 hrs. giving 15 g (84%) which melted with decomposition at 52°-3° C. IR analysis showed peaks at 1730/cm (C=O) and 1520/cm (C--N--H). NMR showed a singlet (9H) at 1 ppm, a doublet (2H, J=6.5 HZ) at 3.3 ppm, a triplet (2H, J=6.5 Hz) at 3.6 ppm, and a triplet (2H, J=6.5 Hz) at 4.2 ppm.

Workup

  1. additionadded to the solution over a ten-minute period
  2. filtrationthe yellow, crystalline precipitate was filtered
  3. washwashed with five 100 ml portions
  4. temperatureof chilled
  5. distillationdistilled water
  6. customThe product was dried in vacuo for 18 hrs
  7. customgiving 15 g (84%) which
  8. custommelted with decomposition at 52°-3° C

Sources & evidence

ORD record
ord-5d225876d9e741cabd85df3fb5a8fe49
Source dataset
uspto-grants-1983_12
Patent number
US04423076

Reaction notes

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