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3,4-Dimethylaniline → HCID 66965558、化合物

HRID 1515058
ノート
印刷プレビュー

反応式

HRID 1515058 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19](O)=[O:20])[CH:15]=2)[C:10]1=[O:22].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:44][C:45]1[CH:46]=[C:47]([CH:49]=[CH:50][C:51]=1[CH3:52])[NH2:48]>CN(C=O)C.O>[CH3:44][C:45]1[CH:46]=[C:47]([NH:48][C:19]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[C:10](=[O:22])[N:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[C:17]3=[O:18])=[O:20])[CH:49]=[CH:50][C:51]=1[CH3:52]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 72483,4-DimethylanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 237358382-(2,6-dichlorophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

生成物 1

HCID 66965558HCID 66965558、化合物

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 2-(2,6-dichlorophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid (403 mg), EDCI (121 mg) and HOBt (135 mg) in DMF (8 mL) was added 3,4-dimethylaniline (53 mg) and the mixture was stirred at room temperature for 24 h. The mixture was poured into water and was extracted with EtOAc. The organic phase was washed with water (3×) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue crystallized from EtOAc to give 2-(2,6-dichlorophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid (3,4-dimethylphenyl)-amide as a pale-yellow solid, mp=238-240° C.; MS (m/z) 439 (M−1); 1H NMR DMSO-d6, 400 MHz) δ 10.49 (s, 1H), 8.62 (s, 1H), 8.50 (d, J=7.83 Hz, 1H), 8.24 (d, J=7.58 Hz, 1H), 7.80 (s, 1H), 7.78 (s, 1H), 7.67 (t, 1H), 7.59 (s, 1H), 7.53 (d, J=8.08 Hz, 1H), 2.24 (s, 3H), 2.21 (s, 3H).

後処理

  1. extractionwas extracted with EtOAc
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue crystallized from EtOAc

出典と根拠

ORDレコード
ord-f4e6e06e89ff4a47b8e9e84613531827
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08222248B2

反応ノート

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