Diethylcarbamoyl chloride → HCID 12175704, compound

HRID 1424751Notes

Reaction equation

HRID 1424751 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[C:14](Cl)=[O:15])[CH3:12]>C1COCC1>[CH2:11]([N:13]([CH2:17][CH3:18])[C:14](=[O:15])[O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([I:3])[CH:5]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 122723-IodophenolHCID 24758Sodium hydride

Product 1

HCID 12175704HCID 12175704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of NaH (1.09 g, 45.47 mmol), in THF (23 mL), a solution of 3-iodophenol (5.00 g, 22.73 mmol), in THF (5.70 mL) was drop wise added at room temperature. After stirring the reaction mixture for 2 h. N,N-diethylcarbamoyl chloride (6.17 g, 45.47 mmol) in THF (8 mL) was added. Stirring was continued for another 8 h. Usual aqueous work up gave the crude carbamate which was purified by column chromatography (eluent: hexane/EtOAc) on silica gel to afford compound b.

Workup

  1. additionwise added at room temperature
  2. stirringStirring
  3. waitwas continued for another 8 h
  4. customUsual aqueous work up gave the crude carbamate which
  5. customwas purified by column chromatography (eluent: hexane/EtOAc) on silica gel

Sources & evidence

ORD record
ord-f22e85bdad824a0e89c3636223e0df0d
Source dataset
uspto-grants-2015_01
Patent number
US08927778B2

Reaction notes

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