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

HRID 564914ノート

反応式

HRID 564914 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d7a80f23e9ae4603b521983d6e3c6d50
出典データセット
uspto-grants-2001_01
特許番号
US06169095A

反応ノート

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