Sulfuric Acid → HCID 131714699, compound

HRID 1981663Notes

Reaction equation

HRID 1981663 reaction equation
[N:1](OCCC(C)C)=[O:2].[CH2:9]([N:12]([CH:19]([OH:34])[C@H:20]1[O:26][C@:24]([CH2:27][CH:28]([CH3:30])[CH3:29])([OH:25])[C@H:23]([OH:31])[C@@H:22]([OH:32])[C@@H:21]1[OH:33])[C:13](=[O:18])[NH:14][CH2:15][CH2:16][Cl:17])[CH2:10][CH3:11].O1CCOCC1.S(=O)(=O)(O)O>CO>[CH2:9]([N:12]([CH:19]([OH:34])[C@H:20]1[O:26][C@:24]([CH2:27][CH:28]([CH3:29])[CH3:30])([OH:25])[C@H:23]([OH:31])[C@@H:22]([OH:32])[C@@H:21]1[OH:33])[C:13](=[O:18])[N:14]([CH2:15][CH2:16][Cl:17])[N:1]=[O:2])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8053Isoamyl NitriteHCID 312751,4-DioxaneHCID 131714700HCID 131714700, compound

Product 1

HCID 131714699HCID 131714699, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isoamyl nitrite (4 ml) was dropped into a solution of the above synthesized 3-n-propyl-3-(isobutyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (3.47 g, 9.06 mmol) in a mixture of methanol (50 ml), dioxane (150 ml), and 10% sulfuric acid (50 ml), with well stirring at 0° to 5° C. After stirring for further 3 hours to complete reaction, which was confirmed by TLC, the reaction mixture was vacuum-concentrated at 25° C. and crystallized from ethanol and water, giving 2.55 g of 3-n-propyl-3-(isobutyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea; yield 68.4%, m.p. 58°-60° C., [α]D20 +71.7° (C 1.0, methanol).

Workup

  1. stirringAfter stirring for further 3 hours to complete reaction, which
  2. concentrationthe reaction mixture was vacuum-concentrated at 25° C.
  3. customcrystallized from ethanol and water

Sources & evidence

ORD record
ord-8e7cef6e25b0493cb6322e01668b9ded
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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