Sodium Nitrite → HCID 131714689, compound

HRID 1981657Notes

Reaction equation

HRID 1981657 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>[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 131714690HCID 131714690, compound

Product 1

HCID 131714689HCID 131714689, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Sodium nitrite fine powder (0.6 g ) was slowly added to a solution of 3-sec-butyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (2.24 g, 5.64 mmol) in formic acid (10 ml) with thorough stirring at 0° to 5° C. spending 1 hour, and stirring was continued for further 2 hours at the same temperature. After confirmation by TLC that the reaction was finished, 20 g of an ion exchange resin (H+ form, registered trade mark: Amberlite IR-120) was added to the reaction mixture at 0° to 5° C., and the mixture was thoroughly 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 1.41 g of 3-sec-butyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea; yield 58.7%, m.p. 68°-70° C., [α]D20 +67.5° (C 1.0, methanol).

Workup

  1. stirringstirring
  2. waitwas continued for further 2 hours at the same temperature
  3. stirringthe mixture was thoroughly 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-923e01a27bc0463aa91d473db64dad32
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

Loading…