Dimethylformamide → HCID 86736663, compound

HRID 426726Notes

Reaction equation

HRID 426726 reaction equation
[N:1]([CH2:4][C@H:5]1[O:11][C:9]([OH:10])=[C:8]([OH:12])[C@@H:7]([OH:13])[CH2:6]1)=[N+:2]=[N-:3].CN(C)C=O.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCOCC.CO>[N:1]([CH2:4][C@H:5]1[O:11][C:9]([OH:10])=[C:8]([OH:12])[C@@H:7]([O:13][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:6]1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86736664HCID 86736664, compound

Product 1

HCID 86736663HCID 86736663, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

Dissolve 7.5 gm. of the azide in 150 ml. of dry dimethylformamide and add 2.5 gm. of sodium hydride. Stir the mixture at 25°C. for 1 hour, then add 10 gm. of benzylbromide and stir the mixture at 25°C. for 6 hours. Add a 20% solution of methanol in ether and filter off the solids and wash with chloroform. Combine the filtrates and pour into water and extract with chloroform and dry over MgSO4. Evaporate the chloroform extract and chromatograph the resultant residue on a silica gel column (110 × 2.5 cm) using 5 % acetone in hexane as the eluant to obtain 6-azido-3-O-benzyl-4,6-dideoxy-D-threo-hex-1-enopyranose.

Workup

  1. dissolutionDissolve 7.5 gm
  2. additionadd 10 gm
  3. filtrationfilter off the solids
  4. washwash with chloroform
  5. additionpour into water
  6. extractionextract with chloroform
  7. dry with materialdry over MgSO4
  8. customEvaporate the chloroform
  9. extractionextract

Sources & evidence

ORD record
ord-c060be4fa4894ba8a7f3e5822c8d58fb
Source dataset
uspto-grants-1979_10
Patent number
US04171356

Reaction notes

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