Sulfuric Acid → N-propyl-N'(beta-D-glucosyl)-N-nitrosourea

HRID 542247

Reaction equation

HRID 542247 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH2:13]([NH:16][C:17]([NH2:19])=[O:18])[CH2:14][CH3:15].[N+:20](NC1C=CC=CC=1)([O-])=[O:21].S(=O)(=O)(O)O>CO>[CH2:13]([N:16]([N:20]=[O:21])[C:17]([NH:19][C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4])=[O:18])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 12303PropylureaHCID 61191N-NitroanilineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 13345998N-propyl-N'(beta-D-glucosyl)-N-nitrosourea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-1 °C

Procedure

A mixture of 3.6 g of D-glucose, 2.3 g of propylurea, 0.2 g of nitroaniline and 0.1 ml of a concentrated sulphuric acid is heated at reflux for 10 minutes in 15 ml of methanol. The residue in the amount of 2.6 g is separated, added with 15 ml of glacial acetic acid, 8 ml of distilled water, 1.8 g of sodium nitrite and stirred at the temperature of -1° C. for 2 hours. The solution is evaporated, the residue is recrystallized from methanol to give 2.32 g (80% of the theoretical) of the product. M.p. 110° C. (decomposition), [α]D -5° (CH3OH), Rf =0.81. Found, %: N 14.12. Calculated, %: N 14.33.

Workup

  1. temperatureis heated
  2. customThe residue in the amount of 2.6 g is separated
  3. additionadded with 15 ml of glacial acetic acid, 8 ml of distilled water, 1.8 g of sodium nitrite
  4. customThe solution is evaporated
  5. customthe residue is recrystallized from methanol
  6. customto give 2.32 g (80% of the theoretical) of the product

Sources & evidence

ORD record
ord-9c9cb849a7f24119a47989326318d543
Source dataset
uspto-grants-1987_04
Patent number
US04656259

Linked notes

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