N,N-Diethylaniline → HCID 22125135, compound

HRID 1858331Notes

Reaction equation

HRID 1858331 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][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.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:33])=O>>[Cl:33][C:7]1[C:6]([CH2:5][NH:4][C:3]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:2]=2[Cl:1])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 22125033HCID 22125033, compound

Product 1

HCID 22125135HCID 22125135, compoundYield 87%

Conditions

Temperature
110 °C

Procedure

A solution of 1.2 g (3.8 mmol) of 5-[2,4-dichloroanilinomethyl]-2-methylthio-3H-pyrimidin-4-one in 40 ml of phosphorus oxychloride was treated with 0.6 ml (3.7 mmol) of N,N-diethylaniline and the mixture was heated at 110° C. for 1 hour, cooled and evaporated. The residue was cautiously partitioned between 40 ml of ice/water and 30 ml of diethyl ether. The aqueous phase was extracted with a further 30 ml of diethyl ether and the combined organic phases were dried over magnesium sulfate, filtered and evaporated to give 1.1 g (87%) of 4-chloro-5-(2,4-dichloroanilinomethyl)-2-methylthiopyrimidine as an oil which slowly solidified to a white solid. [Mass spectrum (ESI) MH+ =334].

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was cautiously partitioned between 40 ml of ice/water and 30 ml of diethyl ether
  4. extractionThe aqueous phase was extracted with a further 30 ml of diethyl ether
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-115e14bd391440249970eb9d3cda7d64
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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