Ethanethiol → 2-(Ethylthio)quinazolin-7-ol

HRID 2079667Notes

Reaction equation

HRID 2079667 reaction equation
[CH2:1]([SH:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].Cl[C:9]1[N:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([O:19]C)=[CH:14][CH:15]=2)[N:10]=1>C(Cl)Cl>[CH2:1]([S:3][C:9]1[N:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=2)[N:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 552514552-Chloro-7-methoxyquinazoline

Product 1

HCID 1360299282-(Ethylthio)quinazolin-7-olYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethanthiol (30 ml) in DCM (50 ml) was added AlCl3 (6 eq). The reaction mixture was cooled to 0° C. and stirred for 10 min under N2 atmosphere. A solution of 2-chloro-7-methoxyquinazoline (1 eq) in DCM (20 ml) was added dropwise to it. The reaction mixture was warmed to room temperature and stirred for 2 h. The solvent was evaporated and residue was partitioned between EtOAc and satd. NaHCO3. The insoluble material was filtered, washed and dried to provide title product as a yellow solid (yield, 60%). The ethyl acetate layer was separated from basic layer, washed with brine and dried over sodium sulfate. Filtration, evaporation and drying under vacuum provide additional amount of product. (yield, 38%). ES/MS m/z 207.0 (MH+).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 2 h
  3. customThe solvent was evaporated
  4. customresidue was partitioned between EtOAc and satd
  5. filtrationThe insoluble material was filtered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-264ef697ae244f0689d4f6d96cb2ccbc
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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