4-Isopropylphenyl isothiocyanate → HCID 16718040, compound

HRID 18147Notes

Reaction equation

HRID 18147 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.[CH:26]([C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[S:37])=[CH:31][CH:30]=1)([CH3:28])[CH3:27]>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:36]([NH:35][C:32]4[CH:33]=[CH:34][C:29]([CH:26]([CH3:28])[CH3:27])=[CH:30][CH:31]=4)=[S:37])=[CH:3][CH:4]=[CH:5][C:6]2=[CH:7]3)[C:13]1=[O:16]

Participants

4

Reactant 2

HCID 1451944-Isopropylphenyl isothiocyanate2×HCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

Product 1

HCID 16718040HCID 16718040, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

300 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.90 mmole) were dissolved in 20 ml of acetonitrile. 309 μl (2 molar equivalents) of 4-isopropylphenyl isothiocyanate was added and the reaction mixture was maintained at room temperature for 16 hours. Two more equivalents of 4-isopropylphenyl isothiocyanate was added and the reaction mixture was again stirred for 24 hours at room temperature. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography (SiO2, CH2Cl2/MeOH 95/5). 428 mg of the desired product (formula shown hereinabove) were isolated as a red powder (yield=93%) which was characterized as follows:

Workup

  1. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-5f6b9d0ccc404d33882b4e682c78f518
Source dataset
uspto-grants-2010_06
Patent number
US07741337B2

Reaction notes

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