Tetrachlorophthalic anhydride → 2,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acid

HRID 27016

반응식

HRID 27016 반응식
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[CH2:16]([N:18]([CH2:26][CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[CH3:25][C:21]1[CH:20]=[C:19]([N:18]([CH2:16][CH3:17])[CH2:26][CH3:27])[CH:24]=[CH:23][C:22]=1[C:11]([C:6]1[C:5]([Cl:13])=[C:4]([Cl:14])[C:3]([Cl:15])=[C:2]([Cl:1])[C:7]=1[C:8]([OH:10])=[O:9])=[O:12]

참가 물질

5

반응물 3

HCID 8326Tetrachlorophthalic anhydrideHCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 1043362,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acid수율 77.3%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

실험 절차

A mixture of tetrachlorophthalic anhydride (21.4 g.), N,N-diethyl-m-toluidine (41 g.), aluminum chloride (30 g.) and o-dichlorobenzene (90 ml.) was heated (75°-95° C.) during one to two hours, then diluted with ice-water. The o-dichlorobenzene layer was separated and steam distilled. The residue was heated with dilute sulfuric acid. The mixture was poured onto ice and made alkaline. The resulting oil was heated in concentrated sulfuric acid. Dilution with water and purification of the product with toluene and hexane afforded 2-(2-methyl-4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (IV: Y2 =CH3, Y'4 =(CH3CH2)2N, Z4 =Z"5 =Z"6 =Z7 =Cl) (26 g., m.p. 117° C. with sublimation).

후처리

  1. temperaturewas heated (75°-95° C.) during one to two hours
  2. customThe o-dichlorobenzene layer was separated
  3. distillationsteam distilled
  4. temperatureThe residue was heated with dilute sulfuric acid
  5. additionThe mixture was poured onto ice
  6. temperatureThe resulting oil was heated in concentrated sulfuric acid
  7. customDilution with water and purification of the product with toluene and hexane

출처 및 근거

ORD 기록
ord-bc1b787f42e34035a981fe1e10eb945e
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220357

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