Water → 3-[2,4-Bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-acetamidophthalide

HRID 1449088노트

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HRID 1449088 반응식
[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[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:15]=2[C:16]([OH:18])=O)=[O:13])=[C:4]1[CH3:24])[CH3:2].[CH3:25][N:26]([CH3:36])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH3:35])[CH3:34])[CH:28]=1.O.[C:38](OC(=O)C)(=[O:40])[CH3:39]>>[CH3:34][N:33]([CH3:35])[C:29]1[CH:28]=[C:27]([N:26]([CH3:36])[CH3:25])[CH:32]=[CH:31][C:30]=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[CH3:24])[C:14]2[C:15](=[CH:19][C:20]([NH:23][C:38](=[O:40])[CH3:39])=[CH:21][CH:22]=2)[C:16](=[O:18])[O:13]1

참가 물질

5

반응물 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 205235662-[(1-Ethyl-2-methyl3-indolyl)carbonyl]-5-aminobenzoic acid

생성물 1

HCID 205235433-[2,4-Bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-acetamidophthalide

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온도
50 °C

실험 절차

A mixture of 3.22 g (0.01 mole) of 2-[(1-ethyl-2-methyl3-indolyl)carbonyl]-5-aminobenzoic acid, 118 g (0.01 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine in 10.0 ml of acetic anhydride was heated to 50° C. for one-half hour. After cooling to ambient temperature, 50 ml of water was added and the reaction mixture was filtered. The filtrate was rendered alkaline with dilute aqueous sodium hydroxide in the presence of 100 ml of toluene. The toluene layer was separated, dried and evaporated to obtain as tan crystals 3-[2,4-bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-acetamidophthalide (Formula III: R°=R1 =R3 =Y1 =H; R2 =NHCOCH3 ; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =CH2CH3) having a melting point of 204°-206° C. Infrared analyses showed maxima at 1733 cm-1 (C=O; s) and 1695 cm-1 (C=O; s). Nuclear magnetic resonance analsis was consistent with the structure. An acetone solution of the above compound developed an intense grape color when spotted on silica gel.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe reaction mixture was filtered
  3. customThe toluene layer was separated
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-d38bff8f74574894b4c859c79ad2d0ad
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04189171

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