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Acetic Anhydride → 3-[2,4-Bis(dimethylamino)phenyl]-3-(1,2-dimethyl-3-indolyl)-4,5,6,7-tetrachlorophthalide

HRID 1660286
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HRID 1660286 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([C:13]2[C:21]([Cl:22])=[C:20]([Cl:23])[C:19]([Cl:24])=[C:18]([Cl:25])[C:14]=2[C:15]([OH:17])=O)=[O:12])=[C:3]1[CH3:26].[CH3:27][N:28]([CH3:38])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:37])[CH3:36])[CH:30]=1.C(OC(=O)C)(=O)C.[OH-].[NH4+]>Cl>[CH3:36][N:35]([CH3:37])[C:31]1[CH:30]=[C:29]([N:28]([CH3:38])[CH3:27])[CH:34]=[CH:33][C:32]=1[C:11]1([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[C:3]=2[CH3:26])[C:13]2[C:14](=[C:18]([Cl:25])[C:19]([Cl:24])=[C:20]([Cl:23])[C:21]=2[Cl:22])[C:15](=[O:17])[O:12]1
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참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 205235362-[(1,2-Dimethyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid

생성물 1

HCID 205235653-[2,4-Bis(dimethylamino)phenyl]-3-(1,2-dimethyl-3-indolyl)-4,5,6,7-tetrachlorophthalide

시약·촉매·용매 1

HCID 313
Hydrochloric Acid
용매

실험 절차

A mixture of 1.55 g (0.0036 mole) of 2-[(1,2-dimethyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid prepared in a manner similar to part A of Example 2, 0.58 g (0.0035 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and ten ml of acetic anhydride was heated to reflux for approximately one hour. After cooling to room temperature, the reaction mixture was poured into 20 ml of 10 percent hydrochloric acid and the mixture then rendered alkaline by the addition of concentrated ammonium hydroxide. The purple solid which separated was collected by filtration, dried, and recrystallized twice from isopropyl acetate to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(1,2-dimethyl-3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: Ro =R1 =R2 =R3 =Cl; R=R5 =R6 =CH3 ; R4 =N(CH3)2 ; Y1 =H) which decomposed at 228°-229° C. The mass spectrum showed an m/e at 575 (M+, 4 Cl). A toluene solution of the product spotted on silica gel developed an intense purple-colored image.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for approximately one hour
  3. customThe purple solid which separated
  4. filtrationwas collected by filtration
  5. customdried
  6. customrecrystallized twice from isopropyl acetate

출처 및 근거

ORD 기록
ord-d98494ecec364ddb9210a52478172880
출처 데이터셋
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04307018

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