m-Chloroperbenzoic acid → HCID 86610340, compound

HRID 1951206Notes

Reaction equation

HRID 1951206 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[N:14]=[C:15]([NH2:27])[S:16][C:17]=1[C:18]1[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([S:25][CH3:26])[N:19]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:26][S:25]([C:20]1[N:19]=[C:18]([C:17]2[S:16][C:15]([NH2:27])=[N:14][C:13]=2[CH3:12])[CH:23]=[C:22]([CH3:24])[N:21]=1)=[O:9]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86610339HCID 86610339, compound

Product 1

HCID 86610340HCID 86610340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (57-86% purity, 6.0 g, 20-30 mmol) is added in portions to a rapidly stirring solution/suspension of 4-methyl-5-(6-methyl-2-methylsulfanyl-pyrimidin-4-yl)-thiazol-2-ylamine (6.0 g, 23.8 mmol) in dry dichloromethane (200 ml) at 0° C. After the addition (15 minutes) the reaction is allowed to warm slowly to room temperature. The mixture is cautiously added to saturated sodium bicarbonate solution (300 ml), shaken, and the organic extract is separated and dried (MgSO4). This first extract contains a 1:1 mixture of sulfoxide and sulfone. The aqueous phase is then partitioned with chloroform to extract the titled compound as yellow solid.

Workup

  1. additionAfter the addition (15 minutes) the reaction
  2. stirringshaken
  3. extractionthe organic extract
  4. customis separated
  5. dry with materialdried (MgSO4)
  6. extractionThis first extract
  7. additiona 1:1 mixture of sulfoxide and sulfone
  8. customThe aqueous phase is then partitioned with chloroform
  9. extractionto extract the titled compound as yellow solid

Sources & evidence

ORD record
ord-16bf29114ab24a6bba7e1f4c6b0d2e66
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

Loading…