Potassium Carbonate → tert-butyl (NE)-N-[(2-chlorophenyl)methylidene]carbamate

HRID 220657Notes

Reaction equation

HRID 220657 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])S(C1C=CC=CC=1)(=O)=O>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:14]=[N:24]/[C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59536806tert-Butyl [(2-chlorophenyl)(phenylsulphonyl)methyl]carbamate

Product 1

HCID 12195069tert-butyl (NE)-N-[(2-chlorophenyl)methylidene]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A quantity of 12.53 g (90.7 mmol) of potassium carbonate was heated through in an HV and then cooled under an argon atmosphere. Quantities of 140 ml of anhydrous THF and 5.77 g (15.1 mmol) of the compound from Example 110A were added and the mixture was stirred under an argon atmosphere at reflux temperature for 16 h. After cooling to RT, the reaction mixture was filtered over celite. The solid was washed with a little THF. The entire filtrate was freed from the solvent on a rotary evaporator. The oily residue was dried in an HV. This gave 3.55 g (98% of theory) of the title compound.

Workup

  1. temperaturecooled under an argon atmosphere
  2. temperatureat reflux temperature for 16 h
  3. filtrationthe reaction mixture was filtered over celite
  4. washThe solid was washed with a little THF
  5. customThe entire filtrate was freed from the solvent on a rotary evaporator
  6. customThe oily residue was dried in an HV

Sources & evidence

ORD record
ord-d05864fdc3fc485e9428b8b59222f87c
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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