Benzene, 1-[(chloromethyl)thio]-4-nitro- → 1-(4-Nitrophenylsulfenyl)methyl-5-chloropyrimidin-2-one

HRID 247076Notes

Reaction equation

HRID 247076 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:20]Cl)=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:20][N:5]2[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]2=[O:9])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 11019967Benzene, 1-[(chloromethyl)thio]-4-nitro-HCID 126485235-Chloropyrimidin-2-ol hydrochloride

Product 1

HCID 201613351-(4-Nitrophenylsulfenyl)methyl-5-chloropyrimidin-2-one

Procedure

The title compound was prepared from 5-chloropyrimidin-2-one hydrochloride (10 mmol) and 4-nitro-1-(chloromethylthio)benzene (10 mmol) in a manner similar to that described in Example 2. The reaction time was 31/2 h. Yield: 1.79 g (60%) of the N- and O-isomers in the ratio 5:2. The O-isomer was extracted from the mixture with chloroform, and the remaining N-isomer, the title compound, was recrystallized from MeOH/HOAc; m.p. 165° C. (Found C44.64; H3.03. Calc. for C11H8ClN3O3S: C44.37; H2.71) 1H NMR (DMSO-d6): δ 5.50 (CH2), 7.4-8.3 (Ph), 8.51 (H-4 and H-6, s). IR (KBr): 1660 cm-1 (CO). MS [70 eV, m/z (% rel. int.)]: 297/299 (5/2,M), 143/145 (100/31).

Workup

  1. custom2 h
  2. extractionThe O-isomer was extracted from the mixture with chloroform
  3. customthe remaining N-isomer, the title compound, was recrystallized from MeOH/HOAc

Sources & evidence

ORD record
ord-f6eb36ed6fbe494b8eb4372f8c7fb196
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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