Sodium Azide → HCID 22672055, compound

HRID 1279627Notes

Reaction equation

HRID 1279627 reaction equation
S(O[CH2:6][C:7]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:8]=1[O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)(C)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:26]([CH2:6][C:7]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:8]=1[O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=[N+:27]=[N-:28]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 22671974HCID 22671974, compound

Product 1

HCID 22672055HCID 22672055, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-(2-mesyloxymethyl-5-chlorophenoxymethyl)benzoate (628 mg; prepared in Reference Example 48.) in DMF (5.0 ml), sodium azide (530 mg) was added in a stream of argon. The mixture was stirred for 40 minutes at 60° C. The reaction mixture was diluted with ethyl acetate. The impurity was filtered with celite. The filtrate was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt =10:1) to give the title compound (404 mg) having the following physical data.

Workup

  1. filtrationThe impurity was filtered with celite
  2. washThe filtrate was washed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe residue was purified on silica gel column chromatography (hexane:AcOEt =10:1)

Sources & evidence

ORD record
ord-d947d087a2d34b9996a7479f10d1a496
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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