Sodium Bicarbonate → 3-(4-Chloro-2-cyanophenyl)-1,1-dimethylurea

HRID 1015786Notes

Reaction equation

HRID 1015786 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])OC2C=CC=CC=2)=[C:4]([C:18]#[N:19])[CH:3]=1.O1CCCC1.[CH3:25][NH:26][CH3:27].C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[N:26]([CH3:27])[CH3:25])=[C:4]([C:18]#[N:19])[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22320367Dimethylamine tetrahydrofuranHCID 66877344Phenyl (4-chloro-2-cyanophenyl)carbamate

Product 1

HCID 140318623-(4-Chloro-2-cyanophenyl)-1,1-dimethylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Step 2) To a solution of phenyl (4-chloro-2-cyanophenyl)carbamate obtained in Step 1 (3.0 g) in tetrahydrofuran (30 ml) was added 2N dimethylamine tetrahydrofuran solution at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into saturated sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→2:3) to give 3-(4-chloro-2-cyanophenyl)-1,1-dimethylurea (2.33 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→2:3)

Sources & evidence

ORD record
ord-fbdfa8d4c9b14e52aaf105d8f3a2f6bb
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

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