Potassium Bromide → 1-(4-Methoxyphenylsulphenyl)methyl-5-chloropyrimidin-2-one

HRID 1982562Notes

Reaction equation

HRID 1982562 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.Cl[CH:11]([S:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)C.[K+].[Br-]>CO>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][CH2:11][N:5]2[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]2=[O:9])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 233169451-Chloroethylthio-4-methoxy benzene

Product 1

HCID 135300981-(4-Methoxyphenylsulphenyl)methyl-5-chloropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The title compound was prepared from 5-chloropyrimidin-2-one hydrochloride (10 mmol) and 1-chloroethylthio-4-methoxy benzene [see Preparation 1](10 mmol) in a manner similar to that described in Example 2. The reaction time was 2 h. Yield: 2.46 g (87%) of the N- and O-isomers in the ratio 7:5. The N-isomer was isolated by its lower solubility in methanol; m.p. 140° C. (MeOH). (Found C41.23; H4.00 Calc. for C12H11ClN2O2S: C50.97; H3.93) 1H NMR (DMSO-d6) 3.77 (OMe), 5.12 (CH2), 6.8-7.4 (Ph), 7.90 and 8.56 (H-4 and H-6, respectively, J 4 Hz). IR (KBr): 1660 cm-1 (CO. MS (70 eV, m/z % rel. int.)]: 282/284 (5/2,M), 143/145 (100/33).

Sources & evidence

ORD record
ord-fb54af9312854de9bd5053677ab72465
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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