Phosgene → 3,6-Dichloro-2-[(4-isocyanatophenoxy)methyl]pyridine

HRID 1288003

반응식

HRID 1288003 반응식
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[C:7]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[N:8][C:9]([Cl:12])=[CH:10][CH:11]=1>C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:7]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]=[C:1]=[O:2])=[CH:17][CH:16]=2)=[N:8][C:9]([Cl:12])=[CH:10][CH:11]=1

참가 물질

4

반응물 2

HCID 6371Phosgene2회HCID 203661734-[(3,6-Dichloropyridin-2-yl)methoxy]aniline

생성물 1

HCID 203661693,6-Dichloro-2-[(4-isocyanatophenoxy)methyl]pyridine

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

Dry toluene (225 ml) was cooled to a temperature of from about 0° to 5° C. and a stream of phosgene gas passed therethrough until 17.4 grams had been absorbed. A solution of 4-((3,6-dichloro-2-pyridinyl)methoxy)benzenamine (15.8 grams; 0.058 mole) in 125 ml. of toluene was added portionwise thereto over a period of about 8 minutes while maintaining the reaction temperature at about 2° to 5° C. The cloudy reaction mixture was then stirred for about 20 minutes with the temperature thereof slowly increasing as excess phosgene was purged from the reaction mixture with nitrogen. At a temperature of about 85° C., the reaction mixture became clear. The toluene solvent was then removed from the reaction mixture under reduced pressure and the residue obtained extracted with hexane. The yellow crystalline product recovered from the hexane extract upon cooling was identified as the desired 3,6-dichloro-2-((4-isocyanatophenoxy)methyl)pyridine compound and was found to have a melting point of 61.5° - 62.5° C.

후처리

  1. customuntil 17.4 grams had been absorbed
  2. temperatureover a period of about 8 minutes while maintaining the reaction temperature at about 2° to 5° C
  3. customThe cloudy reaction mixture
  4. customwas purged from the reaction mixture with nitrogen
  5. customAt a temperature of about 85° C.
  6. customThe toluene solvent was then removed from the reaction mixture under reduced pressure
  7. customthe residue obtained
  8. extractionextracted with hexane
  9. customThe yellow crystalline product recovered from the hexane
  10. extractionextract
  11. temperatureupon cooling

출처 및 근거

ORD 기록
ord-195e128c0e084e7d82bb418fdd9ea327
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03987050

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