Dichloromethane → HCID 22274506, compound

HRID 494881Notes

Reaction equation

HRID 494881 reaction equation
CS(O)(=O)=O.CS(O[CH2:11][CH2:12][C:13]1[O:14][C:15]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)=[CH:18][C:16]=2[CH:17]=1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+].ClCCl>CN(C=O)C>[N:30]([CH2:11][CH2:12][C:13]1[O:14][C:15]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)=[CH:18][C:16]=2[CH:17]=1)=[N+:31]=[N-:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6395Methanesulfonic AcidHCID 33557Sodium AzideHCID 113936782-[5-(4-cyanophenyl)-1-benzofuran-2-yl]ethyl Methanesulfonate

Product 1

HCID 22274506HCID 22274506, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonic acid (109 mg, 0.32 mmol), the product from Example 1C and sodium azide (83 mg, 1.28 mmol) was stirred in DMF for 4 days, then poured into dichloromethane and washed with water. The crude product was purified by flash chromatography, eluting with 2:1 dichloromethane/hexane to provide the title compound as a clear syrup (65 mg, 71%).

Workup

  1. washwashed with water
  2. customThe crude product was purified by flash chromatography
  3. washeluting with 2:1 dichloromethane/hexane

Sources & evidence

ORD record
ord-73162d7cd6424f96bc0a8e9b616b146d
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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