Dimethylformamide → Benzylurea
Reaction equation
S(OC[C@H](CC1C=CC=CC=1)[NH:8][C:9]([O:11]CC1C=CC=CC=1)=O)(=O)(=O)C.[H-].[Na+].S([C:36]1[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=1)(OCC1OC1)(=O)=O.C[N:44](C=O)C>>[CH2:40]([NH:44][C:9]([NH2:8])=[O:11])[C:39]1[CH:38]=[CH:37][CH:36]=[CH:42][CH:41]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Allyl urea 1 (195.2 mg, 0.09 mmol) was dissolved in 6.0 mL of DMF and cooled to 0° C. This was followed by the addition of NaH (54 mg, 1.0 mmol). The glycidyl tosylate (410 mg, mmol) was then added as a solid. The reaction was stirred for 4 hours at 25° C. and then quenched by the addition of 4 mL of saturated aqueous sodium bicarbonate. The reaction was then extracted by 10 mL of Et2O. The organic layer was then washed by 10 mL of saturated aqueous sodium bicarbonate and 2×10 mL of saturated brine. The combined organic portions were then dried over MgSO4, filtered and concentrated in vacuo to provide the desired epoxide 2 (180 mg, 73% yield). The epoxide was then used without further purification. ##STR337##
Workup
- customquenched by the addition of 4 mL of saturated aqueous sodium bicarbonate
- extractionThe reaction was then extracted by 10 mL of Et2O
- washThe organic layer was then washed by 10 mL of saturated aqueous sodium bicarbonate and 2×10 mL of saturated brine
- dry with materialThe combined organic portions were then dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-00e56115630b4952b482de9f055dda3f
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05945413
Reaction notes
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