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Tetrahydrofuran → 1-(1-Methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea

HRID 1451202
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HRID 1451202 반응식
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.Cl[S:13]([N:16]=C=O)(=[O:15])=[O:14].[CH3:19][N:20]1[CH2:24][C:23](=[O:25])[N:22]([CH2:26][CH2:27][CH3:28])[C:21]1=N.C([N:32]([CH2:35]C)CC)C.[O:37]1CCCC1>>[CH3:19][N:20]1[CH2:24][C:23](=[O:25])[N:22]([CH2:26][CH2:27][CH3:28])[CH:21]1[S:13]([N:16]=[N:32][C:35]([NH:1][C:2]1[N:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[N:7]=1)=[O:37])(=[O:14])=[O:15]
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참가 물질

6

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HCID 8028Tetrahydrofuran2회HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 542389381-Methyl-3-n-propyl-2-iminoimidazolidin-4-one

생성물 1

HCID 537527941-(1-Methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea

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온도
0 °C

실험 절차

1.16 g (7.5 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 20 ml of dry tetrahydrofuran, and 1.07 g (7.5 mmol) of chlorosulfonyl isocyanate was dropwise added thereto at -40° C. The reaction temperature was raised to 0° C., and then the reaction mixture was cooled again to -40° C. Then, a mixture comprising 1.16 g (7.5 mmol) of 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one, 0.83 g (8.2 mmol) of triethylamine and 20 ml of dry tetrahydrofuran, was added thereto. The reaction temperature was raised to room temperature, and the mixture was further stirred at the same temperature for 2 hours. Then, the solvent was distilled off under reduced pressure, and then 100 ml of water was added to the obtained residue. The mixture was extracted three times with 100 ml of chloroform. Then, the chloroform layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and precipitated crystals were washed with a solvent mixture of ethyl ether/acetonitrile and collected by filtration to obtain 0.16 g of desired 1-(1-methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea. Melting point: 96°-98° C.

후처리

  1. customat -40° C
  2. temperaturethe reaction mixture was cooled again to -40° C
  3. temperatureThe reaction temperature was raised to room temperature
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. addition100 ml of water was added to the obtained residue
  6. extractionThe mixture was extracted three times with 100 ml of chloroform
  7. washThen, the chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customprecipitated crystals
  11. washwere washed with a solvent mixture of ethyl ether/acetonitrile
  12. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-a36ac14a0e1d4606a16b800bdff9eb5c
출처 데이터셋
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05604179

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