Dimethylformamide → HCID 22808781, compound

HRID 426723Notes

Reaction equation

HRID 426723 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:16]([CH2:19][C@H:20]1[O:25][CH:24]=[CH:23][C@@H:22]([OH:26])[C@@H:21]1[OH:27])=[N+:17]=[N-:18]>C(O)C>[N:16]([CH2:19][C@H:20]1[O:25][CH:24]=[CH:23][C@@H:22]([O:26][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:21]1[O:27][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[N+:17]=[N-:18]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 86736661HCID 86736661, compound

Product 1

HCID 22808781HCID 22808781, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Suspend 5.16 gm. of sodium hydride in 50 ml. of ahydrous dimethylformamide. Maintain the temperature at 0°C. and add 12.4 ml. of benzyl chloride, then 4.65 gm. of 6-azido-6-deoxy-D-glucal in 17 ml. of dimethylformamide. Stir for 4 hours and then add 15 ml. of ethanol, after a further 10 minutes, pour the reaction mixture on ice and then extract wth chloroform. Wash the extracts with water, then dry over MgSO4 and then reduce in vacuo. Chromatograph the residue on silica gel using 25% ethyl acetate in benzene as the eluant to obtain 6-azido-6-deoxy-3,4-di-O-benzyl-D-glucal, [α]26 D + 34.3° (EtOH); pmr (CDCl3)δ 3.52 (2H, m, -CH2N3), 4.6 (4H, m, Ar-CH2 -), 6.38 (1H, dd, J=1.5, 6-Hz, H-1); ν max (CHCl3) 2100, 1640 cm-1.

Workup

  1. additionadd 12.4 ml
  2. additionadd 15 ml
  3. additionpour the reaction mixture on ice
  4. extractionextract wth chloroform
  5. washWash the extracts with water
  6. dry with materialdry over MgSO4

Sources & evidence

ORD record
ord-3e4aed2a3a56461e998470e9f28234df
Source dataset
uspto-grants-1979_10
Patent number
US04171356

Reaction notes

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