2-Bromo-1,1-dimethoxyethane → HCID 68292580, compound

HRID 1504975Notes

Reaction equation

HRID 1504975 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13](=[S:15])[NH2:14])=[N:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:17][CH:18](OC)OC.C([O-])(O)=O.[Na+]>COCCOC.Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[S:15][CH:17]=[CH:18][N:14]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 516892Sodium BicarbonateHCID 86711812HCID 86711812, compound

Product 1

HCID 68292580HCID 68292580, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound 137 (2.1 g, 9.3 mmol) and 2-bromo-1,1-dimethoxyethane (6.31 g, 37.3 mmol) in DME (100 mL) was added dropwise 10 drops of the concentrated HCl at room temperature. The reaction mixture was stirred at 90° C. for 5 h, treated aq. NaHCO3 and extracted with DCM. The combined organic layers was washed with brine (30 mL), dried over Na2SO4, concentrated and purified with silica gel column chromatography (PE:EtOAc=3:1) to give compound 138 (1.8 g, 76%) as a white solid. 1H NMR (400 MHz, CDCl3) δ9.33-9.38 (m, 1H), 8.34-8.40 (m, 1H), 7.65-7.70 (m, 1H), 7.32-7.36 (m, 1H), 7.18-7.23 (m, 1H), 3.12 (t, 2H, J=7.6 Hz), 3.03 (d, 2H, J=7.2 Hz), 2.25-2.35 (m, 2H).

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers was washed with brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified with silica gel column chromatography (PE:EtOAc=3:1)

Sources & evidence

ORD record
ord-de283f61025e48849df9c3d29915fd41
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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