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

HRID 1449084
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1449084
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[C:22]([Cl:23])=[C:21]([Cl:24])[C:20]([Cl:25])=[C:19]([Cl:26])[C:15]=2[C:16]([OH:18])=[O:17])=O)=[C:4]1[CH3:27])[CH3:2].[CH3:28][N:29]([CH3:39])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N:36]([CH3:38])[CH3:37])[CH:31]=1.C(OC(=O)C)(=O)C>C1C=CC=CC=1>[CH3:37][N:36]([CH3:38])[C:32]1[CH:31]=[C:30]([N:29]([CH3:39])[CH3:28])[CH:35]=[CH:34][C:33]=1[C:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:1][CH3:2])[C:4]=2[CH3:27])[C:14]2[C:15](=[C:19]([Cl:26])[C:20]([Cl:25])=[C:21]([Cl:24])[C:22]=2[Cl:23])[C:16](=[O:18])[O:17]1
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Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 197638051-Ethyl-2-methyl-3-(2-carboxy-3,4,5,6-tetrachlorobenzoyl)indole

Produkt 1

HCID 205235643-[2,4-Bis(dimethylamino)-phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalideAusbeute 12,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241
Benzene
Lösungsmittel

Versuchsvorschrift

A stirred mixture of 8.86 g of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid, prepared as described in part A above, 4.0 g of N,N,N',N'-tetramethyl-m-phenylenediamine, and 10.0 ml of acetic anhydride was heated at reflux for a period of three hours. The reaction was then allowed to cool to room temperature, and the tan precipitate which formed was filtered an washed with isopropanol. The material thus obtained was dissolved in 500 ml of benzene and the resulting solution extracted with 70 ml of 10 percent aqueous sodium hydroxide. The benzene solution was filtered and evaporated to dryness at ambient temperature yielding 1.5 g of 3-[2,4-bis(dimethylamino)-phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: R°=R1 =R2 =R3 =Cl; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =CH2CH3 ; Y1 =H), a white solid which melted with decomposition at 227°-229° C. A significant infrared maximum occurred at 1770 cm-1 (C=O; s). The nuclear magnetic resonance spectrum was in complete agreement with the assigned structure. A benzene solution of this product spotted on silica gel developed an intense purple color.

Aufarbeitung

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for a period of three hours
  4. customthe tan precipitate which formed
  5. filtrationwas filtered
  6. washan washed with isopropanol
  7. customThe material thus obtained
  8. extractionthe resulting solution extracted with 70 ml of 10 percent aqueous sodium hydroxide
  9. filtrationThe benzene solution was filtered
  10. customevaporated to dryness at ambient temperature

Quellen und Nachweise

ORD-Eintrag
ord-c70c4340cf7d4f419a70df104ff72810
Quelldatensatz
uspto-grants-1980_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04189171

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