Ammonia → Aclonifen

HRID 1633190

반응식

HRID 1633190 반응식
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]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 996Phenol2회HCID 14798Sodium Hydroxide2회HCID 286972,3,4-Trichloronitrobenzene

생성물 1

HCID 92389Aclonifen

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
50 °C

실험 절차

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% of weight solution of sodium hydroxide solution was 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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9e0fc5d283f47b8b26887d5a63364b3
출처 데이터셋
uspto-grants-1984_10
특허 번호
USRE031717

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