Hydrazine → HCID 54243084, compound

HRID 2397476Notes

Reaction equation

HRID 2397476 reaction equation
[NH2:1][NH2:2].[OH-].[Na+].[CH2:5]([O:12][C@H:13]([C@H:16]([C@@H:25]([C@@H:34]([CH2:36][O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[OH:35])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:14]=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO.O1CCCC1>[NH:1]([C:14]([C@@H:13]([C@H:16]([C@@H:25]([C@@H:34]([CH2:36][O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[OH:35])[O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:12][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:15])[NH2:2]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 10940501HCID 10940501, compound

Product 1

HCID 54243084HCID 54243084, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1.77 g (55.5 mmoles) of anhydrous hydrazine (which has been twice distilled over NaOH) are dissolved in 3 ml of absolute methanol and the solution is cooled in an ice bath. While stirring 3.0 g (5.55 mmoles) of 2,3,4,6-tetra-O-benzyl-D-glucose dissolved in 15 ml of absolute tetra-hydrofuran were added dropwise. After a few minutes the ice bath is removed and the solution is heated to 50° C. At this temperature the mixture is stirred for 7 days in closed flasks. Following this the excess hydrazine is drawn off with the solvent at room temperature in a rotary evaporator. For removal of the last traces of hydrazine the substance is dried for 48 hours with an oil pump running. A colorless viscous sirup remained, yield: 3.05 g (100%).

Workup

  1. temperaturethe solution is cooled in an ice bath
  2. additionwere added dropwise
  3. customAfter a few minutes the ice bath is removed
  4. customis drawn off with the solvent at room temperature in a rotary evaporator
  5. customFor removal of the last traces of hydrazine the substance
  6. customis dried for 48 hours with an oil pump running

Sources & evidence

ORD record
ord-e7bceec536df4b798600f7f79057f657
Source dataset
uspto-grants-1977_05
Patent number
US04021542

Reaction notes

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