Phenylacetyl chloride → HCID 21889951, compound

HRID 721921Notes

Reaction equation

HRID 721921 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][N:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.[C:33]1([CH2:39][C:40]([N:42]=[C:43]=[S:44])=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.C(O)C>[C:33]1([CH2:39][C:40]([N:42]=[C:43]=[S:44])=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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][N:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:43]([NH:42][C:40](=[O:41])[CH2:39][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[S:44])=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 12454157Phenylacetyl isothiocyanate

Product 2

HCID 12454157Phenylacetyl isothiocyanateHCID 21889951HCID 21889951, compoundYield 48%

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-quinazolinyl)oxy]aniline (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 (38 mg, yield 48%).

Workup

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

Sources & evidence

ORD record
ord-6007fa601f674c56ab6c5b9d24e35667
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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