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

HRID 1449088ノート

反応式

HRID 1449088 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
50 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d38bff8f74574894b4c859c79ad2d0ad
出典データセット
uspto-grants-1980_02
特許番号
US04189171

反応ノート

読み込み中…