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

HRID 447874Notes

Reaction equation

HRID 447874 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-9f617503f4324a6cb8030ce454dd7d91
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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