Phosphorus oxychloride → 4-Chloro-5-(2,6-dichloroanilinomethyl)-2-methylthiopyrimidine

HRID 1858315Notes

Reaction equation

HRID 1858315 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[NH:4][CH2:5][C:6]1[C:7](=O)[NH:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:7]1[C:6]([CH2:5][NH:4][C:3]2[C:2]([Cl:1])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:19])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22125077HCID 22125077, compound

Product 1

HCID 221250524-Chloro-5-(2,6-dichloroanilinomethyl)-2-methylthiopyrimidineYield 22%

Conditions

Temperature
100 °C

Procedure

13.6 g (43 mmol) of crude 5-(2,6-dichloroanilinomethyl)-2-methylthio-3H-pyrimidin-4-one was treated with 120 ml of phosphorus oxychloride and the mixture heated at 100° C. for 15 minutes then cooled. The mixture was evaporated and cautiously partitioned between 200 ml of ethyl acetate and 200 ml of water. The organic phase was dried over magnesium sulfate, filtered and evaporated. The product was purified by flash chromatography on silica gel eluting with diethyl ether/isohexane in a ratio of 1:9 to give 3.2 g (22%) of 4-chloro-5-(2,6-dichloroanilinomethyl)-2-methylthiopyrimidine as a pale yellow oil. [Mass spectrum (ESI) MH+ =334].

Workup

  1. temperaturethen cooled
  2. customThe mixture was evaporated
  3. customcautiously partitioned between 200 ml of ethyl acetate and 200 ml of water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by flash chromatography on silica gel eluting with diethyl ether/isohexane in a ratio of 1:9

Sources & evidence

ORD record
ord-c8f7a8a58f324eb3902d911e187dfab3
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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