m-Chloroperbenzoic acid → HCID 69198607, compound

HRID 750799Notes

Reaction equation

HRID 750799 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:5][N:4]=1.Cl[C:25]1C=CC=C(C(OO)=O)C=1.[S:35](=[O:38])(O)[O-:36].[Na+]>C(Cl)Cl>[CH3:25][S:35]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:5][N:4]=1)(=[O:38])=[O:36]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 597539142-Methylthio-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

Product 1

HCID 69198607HCID 69198607, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 25 mL round bottom flask fitted with a stir bar was added 2-methylthio-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine (Reference Example 3) (762 mg, 2 mmol) and 10 mL DCM. The flask was cooled to 0° and a slight excess of m-chloroperbenzoic acid (70%) (1.0 g, 4 mmol) was slowly added and stirred overnight at room temperature. The reaction was worked up by adding 1.0M sodium bisulfite (3 mL), 25 mL more of DCM and the reaction was stirred vigorously to destroy any excess peracid. After washing with 1.0 M sodium bicarbonate, the DCM layer was dried over MgSO4. Filtering the mixture and reducing the solvent volume under reduced pressure gave the desired product which was 97% pure by LC. This was used without further purification. HPLC/MS: m/e=415 (M+); Rt=3.68 min; 1H-NMR 500 MHz (CDCl3): δ 3.46 (s, 3H), 7.08 (d, J=9 Hz, 2H), 7.31-7.4 (m, 5H), 9.00 (s, 1H).

Workup

  1. customIn a 25 mL round bottom flask fitted with a stir bar
  2. temperatureThe flask was cooled to 0°
  3. stirringthe reaction was stirred vigorously
  4. customto destroy any excess peracid
  5. washAfter washing with 1.0 M sodium bicarbonate
  6. dry with materialthe DCM layer was dried over MgSO4
  7. filtrationFiltering the mixture

Sources & evidence

ORD record
ord-02c1975070ee4497b29b76dfe9e8d3f2
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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