Water → HCID 53315311, compound

HRID 1896223Notes

Reaction equation

HRID 1896223 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH:16]=[CH:15][S:14]2)=[CH:9][CH:8]=1.O>CN(C=O)C>[N:1]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[CH:16]=[CH:15][S:14]2)=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 53315308HCID 53315308, compound

Product 1

HCID 53315311HCID 53315311, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (6.0 mg, 0.0923 mmol) was added to a solution of 2-(4-bromomethylphenyl)isothiazol-3-one 31 (18.2 mg, 0.0674 mmol) in DMF (1 mL) and stirred for 20 h at room temperature. Water (10 mL) was added and the mixture was extracted with diethyl ether. The combined organic layer was dried (MgSO4), filtered and evaporated. The residue was purified on flash silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1), afforded the desired compound 32 (11.7 mg, 75%). 1H-NMR (CDCl3, 300 MHz) δ 4.38 (s, 2H), 6.34 (d, J=6.3 Hz, 1H), 7.41 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 8.17 (d, J=6.3 Hz, 1H). HRMS: Found 233.0496. Calcd for C10H9N4OS (M+H)+233.0497.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe combined organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified on flash silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-fbd301cfc94b478b81086d3f69bf4c5f
Source dataset
uspto-grants-2013_08
Patent number
US08518957B2

Reaction notes

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