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

HRID 18144Notes

Reaction equation

HRID 18144 reaction equation
[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.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[S:35])=[CH:29][CH:28]=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:34]([NH:33][C:30]4[CH:31]=[CH:32][C:27]([Br:26])=[CH:28][CH:29]=4)=[S:35])=[CH:3][CH:4]=[CH:5][C:6]2=[CH:7]3)[C:13]1=[O:16]

Participants

4

Reactant 2

HCID 161334-Bromophenyl isothiocyanateHCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

Product 1

HCID 167179891-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[4-bromophenyl]thiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.30 mmole) were dissolved in 6 ml of acetonitrile. 128 μl (2 molar equivalents) of 4-bromophenyl 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). 147 mg of the desired product (formula shown hereinabove) were isolated as a red powder (yield=90%) which was characterized as follows:

Workup

  1. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-98203784e98441568027208365da6532
Source dataset
uspto-grants-2010_06
Patent number
US07741337B2

Reaction notes

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