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Water → 4,6-Bis(difluoromethoxy)-2-(methylsulfanyl)pyrimidine

HRID 2309107
Notes
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Reaction equation

HRID 2309107 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:9]=[C:8]([OH:10])[N:7]=[C:6]([S:11][CH3:12])[N:5]=1.O.O1CCOCC1.Cl[CH:22]([F:24])[F:23]>[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>[F:13][CH:2]([F:1])[O:3][C:4]1[CH:9]=[C:8]([O:10][CH:22]([F:24])[F:23])[N:7]=[C:6]([S:11][CH3:12])[N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 312751,4-DioxaneHCID 178503558HCID 178503558, compound

Product 1

HCID 110434274,6-Bis(difluoromethoxy)-2-(methylsulfanyl)pyrimidineYield 86.7%

Reagents, catalysts & solvents 2

HCID 28557
18-Crown-6
Catalyst
HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

14.0 g (0.067 mole) of 4-difluoromethoxy-6-hydroxy-2-methylthiopyrimidine are suspended in 18 ml of 50% potassium hydroxide solution, 10 ml of water and 160 ml of dioxane. After the addition of 0.5 g of 18-crown-6, the reaction mixture is heated to 40° C., and 20 g of chlorodifluoromethane are subsequently introduced over 5 hours. The aqueous phase is then separated and the organic phase is distilled under a high vacuum, affording 15.0 g (86.4% of theory) of 4,6-bis-difluoromethoxy-2-methylthiopyrimidine with a boiling point of 63° C./0.06 mbar. The substance melts at 46°-48° C.

Workup

  1. customThe aqueous phase is then separated
  2. distillationthe organic phase is distilled under a high vacuum

Sources & evidence

ORD record
ord-06b35c91d2a340f78aee0780c3f9c475
Source dataset
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04692524

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes