4-(Trifluoromethyl)phenyl isothiocyanate → 1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-trifluoromethylphenyl]thiourea

HRID 18155

反応式

HRID 18155 の反応式
[NH2:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:9]4[C:14]=2[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:11](=[O:22])[C:10]=4[CH:23]=[CH:24][CH:25]=3)[CH:5]=[CH:4][CH:3]=1.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[S:36])=[CH:30][CH:29]=1>C(#N)C>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][N:12]1[C:11](=[O:22])[C:10]2[CH:23]=[CH:24][CH:25]=[C:8]3[C:9]=2[C:14](=[C:15]2[C:2]([NH:1][C:35]([NH:34][C:31]4[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:37])[F:38])=[CH:33][CH:32]=4)=[S:36])=[CH:3][CH:4]=[CH:5][C:6]2=[CH:7]3)[C:13]1=[O:16]

参加物

4

反応物 2

HCID 1371344-(Trifluoromethyl)phenyl isothiocyanateHCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

生成物 1

HCID 167180971-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-trifluoromethylphenyl]thiourea収率 90.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

200 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.60 mmole) were dissolved in 10 ml of acetonitrile. 244 mg (2 molar equivalents) of 4-(trifluoromethyl)phenyl isothiocyanate was added and the reaction mixture was maintained at room temperature for 16 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography (SiO2, CH2Cl2/MeOH 95/5). 290 mg of the desired product (formula shown hereinabove) were isolated as a red powder (yield=90%) which was characterized as follows:

後処理

  1. customThe solvent was then evaporated under reduced pressure

出典と根拠

ORDレコード
ord-2eec70619d364fb78576e272b811b333
出典データセット
uspto-grants-2010_06
特許番号
US07741337B2

関連ノート

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