Water → HCID 91154351, compound

HRID 404874Notes

Reaction equation

HRID 404874 reaction equation
Cl[CH:2]([C:7]1[S:11][C:10]([C:12]2[S:16][C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)=[N:14][CH:13]=2)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].[N-:28]=[N+:29]=[N-:30].[Na+].O>CN(C)C=O>[N:28]([CH:2]([C:7]1[S:11][C:10]([C:12]2[S:16][C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)=[N:14][CH:13]=2)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4])=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 69434701HCID 69434701, compound

Product 1

HCID 91154351HCID 91154351, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 5C (0.6 g, 0.0013 mol) and sodium azide (1.0 g, 0.013 mol) in N,N-dimethylformamide was heated at 80° C. under nitrogen for 4 hours. Water was added and the solution was extracted with ether. The organic layer was then washed with brine, dried and filtered. The filtrate was concentrated to give 0.5 g of crude as a yellow oil, which was purified on silica gel (10˜30% ethyl acetate in hexane) to give 0.41 g of pure product as a light yellow oil (72% yield), 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=5.88 Hz, 6H) 4.44-4.61 (m, 1H) 5.10 (q, J=6.62 Hz, 1H) 6.87-6.96 (m, 2H) 6.97 (d, J=3.68 Hz, 1H) 7.08-7.14 (m, 1H) 7.16-7.24 (m, 2H) 7.32 (s, 1H).

Workup

  1. extractionthe solution was extracted with ether
  2. washThe organic layer was then washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give 0.5 g of crude as a yellow oil, which
  7. customwas purified on silica gel (10˜30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1b787bf4bcaf4329b8eb4ade40f8d274
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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