Dimethylformamide → HCID 76374749, compound

HRID 2269327Notes

Reaction equation

HRID 2269327 reaction equation
CN(C)C=O.OC1C=CC(S([N:16]2[CH2:22][CH2:21][CH:20]3[CH2:23][CH:17]2[C:18](=[O:24])[O:19]3)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C(OCC)(=O)C>[CH:17]12[CH2:23][CH:20]([O:19][C:18]1=[O:24])[CH2:21][CH2:22][NH:16]2

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 18333636HCID 18333636, compound

Product 1

HCID 76374749HCID 76374749, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a dimethylformamide (0.6 mL) solution of 2-(4-Hydroxy-benzenesulfonyl)-6-oxa-2-aza-bicyclo[3.2.1]octan-7-one (101.1 mg) and cesium carbonate (331.3 mg) is added the aryl halide (2.5 equiv). The reaction is heated to 50° C. with shaking for 12-24 hours. The sample is cooled, diluted with water and ethyl acetate, and extracted two times with ethyl acetate. The organic layers are combined, dried over sodium sulfate and concentrated. The product is precipitated from diethyl ether to give the Aryloxy-benzenesulfonyl)-6-oxa-2-aza-bicyclo[3.2.1]octan-7-one.

Workup

  1. temperatureThe sample is cooled
  2. extractionextracted two times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product is precipitated from diethyl ether

Sources & evidence

ORD record
ord-4a6fbdc7dcce4a94b6989b60022cc131
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

Loading…