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

HRID 1415123

反応式

HRID 1415123 の反応式
[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

参加物

4

反応物 2

HCID 6371Phosgene2 回HCID 203661734-[(3,6-Dichloropyridin-2-yl)methoxy]aniline

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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 has 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.

後処理

  1. customuntil 17.4 grams has 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

出典と根拠

ORDレコード
ord-c9823eaf1c344153b4b0d853f0010af4
出典データセット
uspto-grants-1977_01
特許番号
US04003906

関連ノート

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