Sodium Hydroxide → phenyl N-[3-(dimethylcarbamoyl)phenyl]carbamate

HRID 726285Notes

Reaction equation

HRID 726285 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[OH-].[Na+].Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17]>O1CCOCC1>[CH3:8][N:7]([CH3:9])[C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:16](=[O:17])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 4247743-Amino-N,N-dimethylbenzamide

Product 1

HCID 297235phenyl N-[3-(dimethylcarbamoyl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 3-amino-N,N-dimethylbenzamide (1.3 g) in 1,4-dioxane(20 ml) was added 1N sodium hydroxide (23.4 ml) and phenyl chloroformate (1.5 ml) successively in an ice-cooled bath. The bath was removed and the reaction mixture was stirred vigorously for 3 hours during which time, phenyl chloroformate (0.7 ml) was further added. The mixture was extracted with ethyl acetate and the organic layer was washed with water and saturated sodium chloride solution. After dried over anhydrous magnesium sulfate and filtered, the solvent was removed in vacuo and the residual oil was purified by flash chromatography eluting with ethyl acetate-n-hexane (2:1, V/V) to give a solid, which was recrystallized from benzene-n-hexane (5:1, V/V) to afford phenyl 3-(dimethylcarbamoyl)phenylcarbamate (1.4 g) as a colorless powder.

Workup

  1. temperaturecooled bath
  2. customThe bath was removed
  3. additionwas further added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated sodium chloride solution
  6. dry with materialAfter dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customthe residual oil was purified by flash chromatography
  10. washeluting with ethyl acetate-n-hexane (2:1, V/V)
  11. customto give a solid, which
  12. customwas recrystallized from benzene-n-hexane (5:1, V/V)

Sources & evidence

ORD record
ord-e527137840b44edab12877e07642505f
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

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