Sodium Nitrite → HCID 131714691, compound

HRID 1981658Notes

Reaction equation

HRID 1981658 reaction equation
[N:1]([O-:3])=O.[Na+].[CH:5]([N:9]([CH:16]([OH:31])[C@H:17]1[O:23][C@@:21]([CH2:24][CH2:25][CH2:26][CH3:27])([OH:22])[C@H:20]([OH:28])[C@@H:19]([OH:29])[C@@H:18]1[OH:30])[C:10](=[O:15])[NH:11][CH2:12][CH2:13][Cl:14])([CH2:7][CH3:8])[CH3:6]>C(O)(=O)C>[CH:5]([N:9]([CH:16]([OH:31])[C@H:17]1[O:23][C@@:21]([CH2:24][CH2:25][CH2:26][CH3:27])([OH:22])[C@H:20]([OH:28])[C@@H:19]([OH:29])[C@@H:18]1[OH:30])[C:10](=[O:15])[N:11]([CH2:12][CH2:13][Cl:14])[N:1]=[O:3])([CH2:7][CH3:8])[CH3:6]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 131714692HCID 131714692, compound

Product 1

HCID 131714691HCID 131714691, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium nitrite (0.85 g) was slowly added to a suspension of 3-sec-butyl-3-(n-butyl β-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (3.25 g, 8.19 mmol) in 80% aqueous acetic acid (40 ml) with thoroughly stirring at 0° to 5° C., and stirring was continued for further 2 hours at the same temperature. After confirmation by TLC that the reaction finished, 15 ml of the same ion exchange resin as mentioned above was added to the reaction mixture at 0° to 5° C., and the mixture was stirred for 30 minutes. The ion exchange resin was filtered off, and the filtrate was vacuum-concentrated at 25° C. and crystallized from methanol and water, giving 2.39 g of 3-sec-butyl-3-(n-butyl β-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea; yield 68.4%, m.p. 92°-95° C. (decomposition). [α]D20 -14.2° (C 1.0, methanol).

Workup

  1. stirringstirring
  2. additionabove was added to the reaction mixture at 0° to 5° C.
  3. stirringthe mixture was stirred for 30 minutes
  4. filtrationThe ion exchange resin was filtered off
  5. concentrationthe filtrate was vacuum-concentrated at 25° C.
  6. customcrystallized from methanol and water

Sources & evidence

ORD record
ord-0e1c9f6dd63845e0922c11da3c65a212
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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