Dimethyl Sulfate → HCID 19894101, compound

HRID 892805Notes

Reaction equation

HRID 892805 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:25]OS(OC)(=O)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:25])[C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 19894075HCID 19894075, compound

Product 1

HCID 19894101HCID 19894101, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

N-tert-butoxycarbonyl-3-aminobenzophenone (2 g, 6.7 mmol) in DMF (15 mL) was added to a suspension of sodium hydride (0.54 g, 13.5 mmol) in DMF (70 mL) and the mixture was stirred at 0° C. for 40 minutes. Dimethylsulfate (1.3 mL, 13.5 mmol) was added and the mixture stirred at room temperature for 15 hours. The mixture was partitioned between ethyl acetate and saturated NaCl. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired material as an orange oil.

Workup

  1. stirringthe mixture stirred at room temperature for 15 hours
  2. customThe mixture was partitioned between ethyl acetate and saturated NaCl
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e12d868bb04465984a80d43387abab7
Source dataset
uspto-grants-1992_06
Patent number
US05120751

Reaction notes

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