Sodium Azide → HCID 86654673, compound

HRID 880460Notes

Reaction equation

HRID 880460 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[CH2:16][CH2:17][N:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[C:19]2[CH3:29])(=O)=O)=CC=1>CN(C)C=O>[N:1]([CH2:16][CH2:17][N:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[C:19]1[CH3:29])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86654672HCID 86654672, compound

Product 1

HCID 86654673HCID 86654673, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium azide (327 mg, 5.02 mmol) was added to a solution of 2-(2-methyl-4-phenyl-pyrrol-1-yl)ethyl 4-methylbenzenesulfonate (1.19 g, 3.35 mmol) in dry dimethylformamide (10 mL) and heated to 90° C. and stirred for 1 h. The reaction mixture was allowed to cool to ambient temperature and partitioned between water (20 mL) and ethyl acetate (25 mL). After stirring for 5 min, the organic layer was separated and washed successively with water (2×30 mL), brine (2×30 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to yield 1-(2-azidoethyl)-2-methyl-4-phenyl-pyrrole (650 mg, 86%) as a brown liquid.

Workup

  1. temperatureto cool to ambient temperature
  2. custompartitioned between water (20 mL) and ethyl acetate (25 mL)
  3. stirringAfter stirring for 5 min
  4. customthe organic layer was separated
  5. washwashed successively with water (2×30 mL), brine (2×30 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c43ad39709c040349b74ba6af7311293
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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