Water → HCID 90411574, compound

HRID 2175972Notes

Reaction equation

HRID 2175972 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH:11]2[N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]1[CH2:9][CH2:10]2)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+].O>CN(C=O)C>[N:21]([CH2:6][CH:7]1[CH2:12][CH:11]2[N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]1[CH2:9][CH2:10]2)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 90412152HCID 90412152, compound

Product 1

HCID 90411574HCID 90411574, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To the title compound of step A (3.4 g, 11.1 mmol) in DMF (15 mL) was added sodium azide (2.1 g, 33.4 mmol). The mixture was heated at 100° C. overnight, cooled to rt, poured into H2O and extracted with DCM. The combined organics were washed with brine and dried (Na2SO4). Purification via silica gel chromatography (10% EtOAc in petroleum ethers) gave the title compound (2.6 g).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with DCM
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customPurification via silica gel chromatography (10% EtOAc in petroleum ethers)

Sources & evidence

ORD record
ord-6fe09d73ac874945b8d36ea35c46a2b7
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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