5-Chlorovaleryl chloride → HCID 21889863, compound

HRID 721945Notes

Reaction equation

HRID 721945 reaction equation
ClCCCCC(Cl)=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]2[O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([N:38]=[C:39]=[S:40])=[O:37]>C1(C)C=CC=CC=1.C(O)C>[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([N:38]=[C:39]=[S:40])=[O:37].[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([NH:38][C:39]([NH:28][C:27]1[CH:29]=[CH:30][C:24]([O:23][C:14]2[C:13]3[C:18](=[CH:19][C:20]([O:21][CH3:22])=[C:11]([O:10][CH3:9])[CH:12]=3)[N:17]=[CH:16][N:15]=2)=[CH:25][CH:26]=1)=[S:40])=[O:37]

Participants

7

Reactant 3

HCID 740895-Chlorovaleryl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 21890661HCID 21890661, compound

Product 2

HCID 21889863HCID 21889863, compoundYield 58%HCID 21890661HCID 21890661, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

5-Chloropentanoyl isothiocyanate was prepared using commercially available 5-chloropentanoyl 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 5-chloropentanoyl 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 (46 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-47739c6746d94790a0a35adc160f0418
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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