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Urea → HCID 22013857, 화합물

HRID 1532728
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HRID 1532728 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[O:11][C:12]([CH3:29])=[C:13]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=O)=[CH:20][CH:19]=2)[N:14]=1.S(Cl)(Cl)=O.[NH2:34][C:35]([NH2:37])=[O:36]>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[O:11][C:12]([CH3:29])=[C:13]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([NH:34][C:35]([NH2:37])=[O:36])=[O:28])=[CH:20][CH:19]=2)[N:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 1176Urea2회HCID 24386Thionyl ChlorideHCID 22013885HCID 22013885, 화합물

생성물 1

HCID 22013857HCID 22013857, 화합물수율 21%

반응 조건

온도
60 °C

실험 절차

To 3-[4-[2-(2-(benzothiophen-2-yl)-5-methyl-4-oxazolyl)ethoxy]phenyl]propionic acid (850 mg, 2.09 mmol) obtained in Example 14 was added thionyl chloride (2 ml, 27.4 mmol) and the mixture was stirred under heating for 40 min at 60° C. The reaction mixture was concentrated and N,N-dimethylaniline (10 ml) was added to the residue. Urea (250 mg, 4.17 mmol) was added and the mixture was stirred under heating for 5 hr at 150° C. Urea (250 mg, 4.17 mmol) was again added and the mixture was heated for 10 hr at 150° C. The reaction mixture was cooled to room temperature and the precipitated solid (468 mg) was collected by filtration. A part (260 mg) thereof was washed successively with water, ethyl acetate/tetrahydrofuran (9:1), 10% aqueous sodium hydroxide solution, 1N hydrochloric acid, water and tetrahydrofuran, and dried to give the title compound (110 mg, yield 21%) as a gray-white solid.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionN,N-dimethylaniline (10 ml) was added to the residue
  3. stirringthe mixture was stirred
  4. temperatureunder heating for 5 hr at 150° C
  5. temperaturethe mixture was heated for 10 hr at 150° C
  6. temperatureThe reaction mixture was cooled to room temperature
  7. filtrationthe precipitated solid (468 mg) was collected by filtration
  8. washA part (260 mg) thereof was washed successively with water, ethyl acetate/tetrahydrofuran (9:1), 10% aqueous sodium hydroxide solution, 1N hydrochloric acid, water and tetrahydrofuran
  9. customdried

출처 및 근거

ORD 기록
ord-a6203b54bb7b43dbb4066c86a2f3d929
출처 데이터셋
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06204277B1

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