Dimethylformamide → HCID 86747564, compound

HRID 1975084Notes

Reaction equation

HRID 1975084 reaction equation
[H-].[Na+].[Br:3][C:4]1[O:9][C:8]2[S:10][C:11]([CH3:15])([CH3:14])[C@H:12](Br)[C:7]=2[C@@H:6](O)[CH:5]=1.[N-:17]=[N+:18]=[N-:19].[Na+].CN(C)C=[O:24]>O>[N:17]([C@H:6]1[CH:5]=[C:4]([Br:3])[O:9][C:8]2[S:10][C:11]([CH3:15])([CH3:14])[C@H:12]([OH:24])[C:7]1=2)=[N+:18]=[N-:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 33557Sodium AzideHCID 67822052HCID 67822052, compound

Product 1

HCID 86747564HCID 86747564, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium hydride, 60% in mineral oil, (134 mg, 3.36 mmol) was added to a solution of 16 (1.15 g, 3.36 mmol) in N,N-dimethylformamide (25 ml) at 0° C. and stirred at rt for 2 h. The reaction was cooled to 0° C. and sodium azide (635 mg, 10.8 mmol) in water (2 ml) was added. After stirring at rt for 1 h, the resultant solution was poured into water (150 ml). The product was extracted with dichloromethane (50 ml), washed several times with water and dried over magnesium sulfate. The solvent was evaporated in vacuo to give the product as a brown oil, 1.0 g (98%), which was used without further purification. 1H NMR (CDCl3): d 1.31 (s, 3 H), 1.48 (s, 3 H), 2.42 (d, J=5.3 Hz, H), 3.72 (d of d, J=7.5 and 5.3 Hz, 1 H), 4.21 (d, J 7.5 Hz, 1 H) and 6,76 (s, 1 H); IR (neat) 3600-3200, 2101, 1663, 1568 and 1470 cm-1 ; MS: m/z 303 MH+).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringAfter stirring at rt for 1 h
  3. extractionThe product was extracted with dichloromethane (50 ml)
  4. washwashed several times with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-56981d52b807426783185b4ae3e359d8
Source dataset
uspto-grants-1994_02
Patent number
US05284857

Reaction notes

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