N-(3-(Dimethylamino)propyl)-N'-phenylthiourea → N-{3-[3-(Dimethylamino)propyl]-5-phenylthiazol-2(3H)-ylidene}aniline

HRID 896611Notes

Reaction equation

HRID 896611 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[S:8].Br[CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:19]=O>CN(C)C=O>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[CH:19]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:8][C:7]1=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 1982459N-(3-(Dimethylamino)propyl)-N'-phenylthioureaHCID 108889012-Bromo-2-phenylacetaldehyde

Product 1

HCID 22350922N-{3-[3-(Dimethylamino)propyl]-5-phenylthiazol-2(3H)-ylidene}anilineYield 53.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using N-[3-(dimethylamino)propyl]-N′-phenylthiourea (650 mg) obtained in Reference Example 3 as described below, 2-bromo-2-phenylacetoaldehyde (600 mg) and N,N-dimethylformamide (11 ml), the title compound (497 mg) was obtained in a similar manner to in Example 1.

Workup

  1. customobtained in Reference Example 3

Sources & evidence

ORD record
ord-151958d84bfa41139bf617ba545663e1
Source dataset
uspto-grants-2005_07
Patent number
US06919361B2

Reaction notes

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