Hydrochloric Acid → N-butyl-N'-(beta-D-glucosyl)-N-nitrosourea

HRID 542248

Reaction equation

HRID 542248 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:17][C:18]([NH2:20])=[O:19])[CH2:14][CH2:15][CH3:16].[N+:21](NC1C=CC=CC=1)([O-])=[O:22].Cl>CO>[CH2:13]([N:17]([N:21]=[O:22])[C:18]([NH:20][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:19])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11595ButylureaHCID 61191N-NitroanilineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 13346001N-butyl-N'-(beta-D-glucosyl)-N-nitrosoureaYield 669.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-1 °C

Procedure

A mixture of 3.6 g of D-glucose, 2.8 g of butylurea, 0.2 g of nitroaniline and 0.15 ml of a concentrated hydrochloric acid in 10 ml of methanol is heated at reflux for 20 minutes. The resulting precipitate in the amount of 3 g is separated and added with 15 ml of glacial acetic acid, 10 ml of distilled water, 1.8 g of sodium nitrite and stirred at the temperature of -1° C. for 2 hours to give 2.98 g of the product (90% of the thoretical), hydroscopic, [α]D -1° (CH3OH), Rf =0.85. Found, %: N 13.47. Calculated, % N 13.68.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 minutes
  3. customThe resulting precipitate in the amount of 3 g is separated
  4. additionadded with 15 ml of glacial acetic acid, 10 ml of distilled water, 1.8 g of sodium nitrite

Sources & evidence

ORD record
ord-7d9ad15dac5d4f31933a8a05d57d8313
Source dataset
uspto-grants-1987_04
Patent number
US04656259

Linked notes

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