Water → HCID 131714693, compound

HRID 1981659Notes

Reaction equation

HRID 1981659 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].Cl.[CH3:8][C:9](=[CH2:27])[CH2:10][NH:11][CH2:12][C@H:13]1[O:23][C@H:17]([O:18]CCCC)[C@H:16]([OH:24])[C@@H:15]([OH:25])[C@@H:14]1[OH:26].[OH2:28]>C(#N)C.C(=O)([O-])[O-].[Ag+2]>[CH3:8][C:9](=[CH2:27])[CH2:10][N:11]([CH:12]([OH:28])[C@H:13]1[O:23][C@:17]([CH2:12][CH2:13][CH2:14][CH3:15])([OH:18])[C@H:16]([OH:24])[C@@H:15]([OH:25])[C@@H:14]1[OH:26])[C:5](=[O:6])[NH:4][CH2:3][CH2:2][Cl:1]

Participants

6

Reactant 3

HCID 962WaterHCID 160352-Chloroethyl isocyanateHCID 70465480HCID 70465480, compound

Product 1

HCID 131714693HCID 131714693, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Chloroethyl isocyanate (1.35 g) and silver carbonate (2.14 g) were added to a solution of n-butyl 6-(2-methyl-2-propenylamino)-6-deoxy-α-D-glucopyranoside hydrochloride (3.47 g, 10.6 mmol) in a mixture of water (25 ml) and acetonitrile (40 ml) at 0° to 5° C., and the mixture was heated under reflux on a water bath for 1 hour. Then, the reaction mixture was filtered while hot to remove the insoluble silver salt. The filtrate was vacuum-concentrated and crystallized from ethanol and water, giving 2.73 g of 3-(2-methyl-2-propenyl)-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea; yield 65.2%, m.p. 110°-112° C., [α]D20 +59.2° (C 1.0, methanol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux on a water bath for 1 hour
  3. filtrationThen, the reaction mixture was filtered while hot
  4. customto remove the insoluble silver salt
  5. concentrationThe filtrate was vacuum-concentrated
  6. customcrystallized from ethanol and water

Sources & evidence

ORD record
ord-4d8c34632df04721bb81da2c6d6e60e5
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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