m-Chloroperbenzoic acid → HCID 178482189, compound

HRID 964844Notes

Reaction equation

HRID 964844 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(O)C>[NH2:1][C:2]1[N+:7]([O-:19])=[C:6]([NH:8][CH3:9])[CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 2354466-Chloro-n4-methylpyrimidine-2,4-diamine

Product 1

HCID 178482189HCID 178482189, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
10 °C

Procedure

4 g of 2-amino-4-methylamino-6-chloropyrimidine are suspended in 50 ml of ethanol. After having cooled to 10° C., 11.9 g of meta-chloroperbenzoic acid are added dropwise as a solution in 100 ml of ethanol. At the end of addition, room temperature is regained and stirring is continued for 3 hours. The reaction mixture is cooled to 5° C. and then filtered on sintered glass. The precipitate obtained is recrystallized from 160 ml of a 2/3-1/3 ethanol-water mixture. 1.60 g of 2-amino-4-methylamino-6-chloropyrimidine 3-oxide are obtained.

Workup

  1. additionAt the end of addition, room temperature
  2. temperatureThe reaction mixture is cooled to 5° C.
  3. filtrationfiltered on sintered glass
  4. customThe precipitate obtained
  5. customis recrystallized from 160 ml of a 2/3-1/3 ethanol-water mixture

Sources & evidence

ORD record
ord-69d696df41ef47e8afa690bde4025709
Source dataset
uspto-grants-1998_06
Patent number
US05772990

Reaction notes

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