alpha,4-Dichloroanisole → 2-(4-Chlorophenoxymethyl)thio-5-chloropyrimidine

HRID 905214Notes

Reaction equation

HRID 905214 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([O:6][CH2:7]Cl)=[CH:4][CH:3]=1.[K].[Cl:12][C:13]1[CH:14]=[N:15][C:16](=[S:19])[NH:17][CH:18]=1>COCCOC>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([O:6][CH2:7][S:19][C:16]2[N:17]=[CH:18][C:13]([Cl:12])=[CH:14][N:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 88801alpha,4-DichloroanisoleHCID 5462222PotassiumHCID 71403455-Chloro-2(1H)-pyrimidinethione

Product 1

HCID 204757412-(4-Chlorophenoxymethyl)thio-5-chloropyrimidineYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of p-chlorophenoxymethyl chloride (6 mmol) and the potassium salt of 5-chloropyrimidine-2-thione (5 mmol) in 1,2-dimethoxyethane (25 ml) was stirred at room temperature for 10 h, the solvent distilled off at reduced pressure, the residue extracted with chloroform (70 ml), the chloroform (70 ml), the chloroform solution washed with 1 M NaOH (2×10 ml) and water (10 ml), and the dried (MgSO4) solution evaporated. The residual sulfide was recrystallized from iPrOH; yield 70%, m.p. 120° C. 1H NMR (DMSO-d6): δ5.90 (SCH2), 6.98 and 7.31 (Ph), 8.78 (H-4, H-6).

Workup

  1. distillationthe solvent distilled off at reduced pressure
  2. extractionthe residue extracted with chloroform (70 ml)
  3. washthe chloroform (70 ml), the chloroform solution washed with 1 M NaOH (2×10 ml) and water (10 ml)
  4. dry with materialthe dried (MgSO4) solution
  5. customevaporated
  6. customThe residual sulfide was recrystallized from iPrOH

Sources & evidence

ORD record
ord-6850c6687dd74eae85231a8410eefbdd
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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