Phenylacetyl chloride → HCID 21890984, compound

HRID 721880Notes

Reaction equation

HRID 721880 reaction equation
C1(CC(Cl)=O)C=CC=CC=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[C:28]([CH3:33])[C:27]=1[CH3:34].[C:35]1([CH2:41][C:42]([N:44]=[C:45]=[S:46])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.C(O)C>[C:35]1([CH2:41][C:42]([N:44]=[C:45]=[S:46])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:45]([NH:44][C:42](=[O:43])[CH2:41][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[S:46])=[C:28]([CH3:33])[C:27]=1[CH3:34]

Participants

7

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 12454157Phenylacetyl isothiocyanateHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 2

HCID 12454157Phenylacetyl isothiocyanateHCID 21890984HCID 21890984, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

2-Phenylethanoyl isothiocyanate was prepared using commercially available 2-phenylethanoyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-phenylethanoyl 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 (44 mg, yield 58%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-280ed331e62c43dc92c519fcf8d549f9
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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