Sodium Nitrite → N-propyl-N'(beta-D-glucosyl)-N-nitrosourea

HRID 1448523Notes

Reaction equation

HRID 1448523 reaction equation
[C@@H:1]1([NH:12][C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[N:19]([O-])=[O:20].[Na+]>O.C(O)(=O)C>[C@@H:1]1([NH:12][C:13]([N:15]([N:19]=[O:20])[CH2:16][CH2:17][CH3:18])=[O:14])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 536598611-(beta-D-glucopyranosyl)-3-n-propylurea

Product 1

HCID 13345998N-propyl-N'(beta-D-glucosyl)-N-nitrosoureaYield 81.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-(β-D-glucopyranosyl)-3-n-propylurea (1.50 g) was dissolved in a mixture of water (10 ml) and acetic acid (2 ml), and to the resulting solution was added 560 mg (1.5 mol. equivalents) of sodium nitrite at ambient temperature under stirring to effect the nitrosation. The reaction mixture was treated with Amberlite IR-120 (H+ form) for the removal of sodium ion and then concentrated to dryness below 35° C. and under a reduced pressure. Crystallisation of the residue from n-propanol gave 1.35 g of the titled compound. Yield 80%. mp. 112° C. (decomposition with foaming). [α]D21 -6° (c 1.0, H2O).

Workup

  1. concentrationconcentrated to dryness below 35° C. and under a reduced pressure
  2. customCrystallisation of the residue from n-propanol

Sources & evidence

ORD record
ord-a4bdb17c62a3449d98cdd1eebaa0d127
Source dataset
uspto-grants-1979_12
Patent number
US04180655

Reaction notes

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