Triethylamine → N-(2-hydroxy-4-nitrophenyl)-N'-(2,3-methylenedioxyphenyl)urea

HRID 323055

반응식

HRID 323055 반응식
[CH2:1]1[O:9][C:8]2[C:3](=[C:4](C(O)=O)[CH:5]=[CH:6][CH:7]=2)[O:2]1.C([N:15]([CH2:18]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][C:39]=1[OH:47]>C1(C)C=CC=CC=1>[OH:47][C:39]1[CH:40]=[C:41]([N+:44]([O-:46])=[O:45])[CH:42]=[CH:43][C:38]=1[NH:37][C:18]([NH:15][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12)=[O:27]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3048321,3-Dioxaindane-4-carboxylic acidHCID 49847212-Amino-5-Nitrophenol

생성물 1

HCID 9883432N-(2-hydroxy-4-nitrophenyl)-N'-(2,3-methylenedioxyphenyl)urea수율 42%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

To a solution of the 2,3-methylenedioxyphenylcarboxylic acid in toluene, triethylamine (0.27 mL, 1.95 mmol) and diphenylphosphoryl azide (DPPA) (0.32, mL, 1.5 mmol) were added. The reaction mixture was stirred at 60° C. for 2 hours, then 2-amino-5-nitrophenol (250 mg, 1.5 mmol) was added. The reaction mixture was stirred at 100° C. for 18 hours. After the reaction mixture was cooled to room temperature, it was partitioned between 5% citric acid and ethyl acetate. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. Chromatography of the resulting solid on silica gel (hexane:ethyl acetate; 5:1) gave product (200 mg, 42%). EI-MS m/z 318 (M+H)+

후처리

  1. stirringThe reaction mixture was stirred at 100° C. for 18 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customit was partitioned between 5% citric acid and ethyl acetate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ef0995265c31454f9a3e3ffc16bdabb9
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211373B1

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