4-(Bromomethyl)benzoic acid → N-{2-[4-(Bromomethyl)phenyl]acetyl}-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea

HRID 721944Notes

Reaction equation

HRID 721944 reaction equation
S(Cl)(Cl)=O.BrCC1C=CC(C(O)=O)=CC=1.BrCC1C=CC(C(Cl)=O)=CC=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1.[Br:49][CH2:50][C:51]1[CH:56]=[CH:55][C:54]([CH2:57][C:58]([N:60]=[C:61]=[S:62])=[O:59])=[CH:53][CH:52]=1>C1(C)C=CC=CC=1.C(O)C>[Br:49][CH2:50][C:51]1[CH:52]=[CH:53][C:54]([CH2:57][C:58]([NH:60][C:61]([NH:46][C:45]2[CH:47]=[CH:48][C:42]([O:41][C:32]3[C:31]4[C:36](=[CH:37][C:38]([O:39][CH3:40])=[C:29]([O:28][CH3:27])[CH:30]=4)[N:35]=[CH:34][CH:33]=3)=[CH:43][CH:44]=2)=[S:62])=[O:59])=[CH:55][CH:56]=1

Participants

8

Reactant 5

HCID 225994-(Bromomethyl)benzoic acidHCID 24386Thionyl ChlorideHCID 50682894-Bromomethyl-benzoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 218907762-[4-(Bromomethyl)phenyl]ethanoyl isothiocyanate

Product 1

HCID 21890304N-{2-[4-(Bromomethyl)phenyl]acetyl}-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 4-(bromomethyl)benzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate was prepared using the resultant 4-(bromomethyl)-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (50 mg, yield 52%).

Workup

  1. customThe solvent was removed by distillation, and 2-[4-(bromomethyl)phenyl]ethanoyl isothiocyanate
  2. customwas prepared
  3. concentrationThe reaction solution was concentrated
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-60dda6893381445e83d4e907f03baa6e
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…