Ammonia → Aclonifen

HRID 1074847

反応式

HRID 1074847 の反応式
Cl[C:2]1[C:7]([Cl:8])=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH3:13].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CS(C)=O.C(O)(=O)C>[Cl:8][C:7]1[C:6]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=[C:3]([N+:10]([O-:12])=[O:11])[C:2]=1[NH2:13]

参加物

7

反応物 4

HCID 222AmmoniaHCID 996Phenol2 回HCID 14798Sodium Hydroxide2 回HCID 286972,3,4-Trichloronitrobenzene

生成物 1

HCID 92389Aclonifen

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

A solution of 911 gm (4 mole) of 2,3,4-trichloronitrobenzene was dissolved in 4 liters of dimethyl sulfoxide and mixed in a 10-liter autoclave with 400 ml of liquid ammonia. The autoclave was closed and kept at 50° C. for 24 hours, a pressure of 5.3 bars being set. After cooling of the mixture and ventilation of the pressure vessel, the mixture was removed and stirred in a 15 liter vessel with 400 gm of 40% (% by weight) sodium hydroxide solution. In so doing, ammonia escaped and was drawn off. Four hundred sixteen grams of phenol (4.4 mol) were then added to the solution which was heated to 50° C., and 440 gm of 40% by weight solution of sodium hydroxide solution were dropped therein. The mixture was stirred for 7 hours at 50°-60° C. To complete the reaction, 41 gm of phenol and 44 gm of 40% by weight solution of sodium hydroxide were added again, and the mixture was kept at 60° C. for a further 3 hours. The mixture was allowed to cool and was acidified with 100 ml of glacial acetic acid, and the product was precipitated with ice water by trituration. The yellowy brown solid crude product was extracted, washed with water, and dried. The crude product (980 gm m.p. 70°-78° C.) was recrystallized from 2.5 liters of isopropanol. The yield was 800 gm (75.5% of theory) of a yellowy brown solid, m.p. 81.5°-83.5° C.

後処理

  1. customThe autoclave was closed
  2. temperatureAfter cooling of the mixture and ventilation of the pressure vessel
  3. customthe mixture was removed
  4. stirringThe mixture was stirred for 7 hours at 50°-60° C
  5. additionwere added again
  6. waitthe mixture was kept at 60° C. for a further 3 hours
  7. temperatureto cool
  8. customthe product was precipitated with ice water by trituration
  9. extractionThe yellowy brown solid crude product was extracted
  10. washwashed with water
  11. customdried
  12. customThe crude product (980 gm m.p. 70°-78° C.) was recrystallized from 2.5 liters of isopropanol

出典と根拠

ORDレコード
ord-e3443f7db6484cdb8075926be07562c3
出典データセット
uspto-grants-1983_07
特許番号
US04394159

関連ノート

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