Potassium Carbonate → 8'-chloro-5'-([methylthio]methoxy)-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one

HRID 33403

Reaction equation

HRID 33403 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[NH:8][C:7]12[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][S:26][CH2:27]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:25][S:26][CH3:27])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[NH:8][C:7]12[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16916Chloromethyl methyl sulfideHCID 9943277HCID 9943277, compound

Product 1

HCID 129855038'-chloro-5'-([methylthio]methoxy)-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 8′-chloro-5′-hydroxy-1′H-spiro[cyclohexane-1,4′-quinazolin]-2′(3′H)-one, which can be prepared according to processes disclosed in example 63 of PCT/EP02/03594 (6 g, 2.25 mmol) in dimethylformamide (6 mL) was added potassium carbonate (0.776 g, 5.6 mmol) and chloromethyl methyl sulfide (0.26 mL, 2.7 mmol). The mixture was stirred in a sealed tube at 100° C. for 3 days. Dimethylformamide was removed by evaporation in vacuo. Water was added to the residue and the aqueous layer was extracted twice with ethyl acetate.

Workup

  1. customDimethylformamide was removed by evaporation in vacuo
  2. additionWater was added to the residue
  3. extractionthe aqueous layer was extracted twice with ethyl acetate

Sources & evidence

ORD record
ord-80b11ab93b1b40e5adca360a41e3dbd5
Source dataset
uspto-grants-2008_09
Patent number
US07429598B2

Linked notes

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