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

HRID 581757노트

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HRID 581757 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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. mp: 151.2-153.0° C.

후처리

  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)

출처 및 근거

ORD 기록
ord-a75146d0101245709560b596a7613146
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922711

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