Phosgene → 7-isocyanato-4-methyl-2H-chromen-2-one

HRID 2061377노트

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HRID 2061377 반응식
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH3:17])=[CH:11][C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.O1CCOCC1>[N:5]([C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH3:17])=[CH:11][C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1)=[C:1]=[O:2]

참가 물질

5

반응물 2

HCID 6371PhosgeneHCID 922497-Amino-4-methylcoumarin

생성물 1

HCID 583781007-isocyanato-4-methyl-2H-chromen-2-one수율 25%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A 200-mL three-neck flask fitted with a dry ice condenser and magnetic stirrer was charged with a solution of 20% phosgene in toluene solution (2.0 mL) and dioxane (80 mL). To this mixture was added 7-amino-4-methyl-2H-chromen-2-one (2.00 g, 11.4 mmol). The mixture was stirred at 100° C. for 12 h. The initial yellow colour disappeared and a white solid precipitated. An additional 20% phosgene in toluene solution (7.0 mL) was added and the mixture heated for an additional 5 h, at which time the solution cleared. Excess phosgene and traces of HCl was removed by bubbling nitrogen gas through the solution. The cloudy solution was filtered to remove unreacted 7-amino-4-methyl-2H-chromen-2-one and concentrated to give 76 (0.5 g, 25%) as a white solid. H1 NMR (500 MHz, CDCl3): δ=7.50 (1H, d, J=7.40 Hz, ArH), 7.46 (2H, s, ArH), 6.20 (1H, s, ArH), 2.35 (3H, s, CH3): ir (CH2CL2) 2314 (N═C═O), 1726 and 1615 cm−1.

후처리

  1. customA 200-mL three-neck flask fitted with a dry ice condenser and magnetic stirrer
  2. customa white solid precipitated
  3. additionAn additional 20% phosgene in toluene solution (7.0 mL) was added
  4. temperaturethe mixture heated for an additional 5 h, at which time the solution
  5. customExcess phosgene and traces of HCl was removed
  6. customby bubbling nitrogen gas through the solution
  7. filtrationThe cloudy solution was filtered
  8. customto remove unreacted 7-amino-4-methyl-2H-chromen-2-one
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4cfcdfbea8074b608028271eb26a4f07
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283340B2

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