Dichloromethane → HCID 59224722, compound

HRID 1811760Notes

Reaction equation

HRID 1811760 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12]C=2)[N:5]=[C:4]([C:16]2C(Cl)=[CH:18][C:19]([Cl:23])=[C:20]([OH:22])[CH:21]=2)[N:3]=1.Cl[CH2:26][Cl:27].ClC1C=CC=C(C(OO)=[O:36])C=1>CO>[NH2:1][C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:10]=[CH:15][CH:14]=[C:13]([OH:36])[CH:12]=2)[N:5]=[C:4]([C:16]2[C:26]([Cl:27])=[CH:18][C:19]([Cl:23])=[C:20]([OH:22])[CH:21]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 57898662HCID 57898662, compound

Product 1

HCID 59224722HCID 59224722, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Amino-6-benzylsulfanyl-[1,3,5]triazin-2-yl)-2,4-dichlorophenol (150 mg) obtained in Step 2 above was placed in a reaction vessel, and then dichloromethane (10 ml) and methanol (2 ml) were added thereto. The mixture was stirred. m-Chloroperbenzoic acid (210 mg) was added to the resulting suspension at room temperature, and stirred for 30 minutes. The resulting mixture was concentrated under reduced pressure. To this, N,N-dimethylformamide (4.5 ml), triethylamine (0.19 ml), and 3-mercaptophenol (0.12 ml) were added and stirred at room temperature for 4 hours. The reaction solution was diluted with ethyl acetate, and then sequentially washed with a saturated aqueous sodium bicarbonate solution and water. The ethyl acetate solution was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane and ethyl acetate) to yield 5-[4-amino-6-(3-hydroxyphenylsulfanyl)-[1,3,5]triazin-2-yl]-2,4-dichlorophenol (54 mg) as a yellow solid.

Workup

  1. stirringstirred for 30 minutes
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionTo this, N,N-dimethylformamide (4.5 ml), triethylamine (0.19 ml), and 3-mercaptophenol (0.12 ml) were added
  4. stirringstirred at room temperature for 4 hours
  5. additionThe reaction solution was diluted with ethyl acetate
  6. washsequentially washed with a saturated aqueous sodium bicarbonate solution and water
  7. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe resulting crude product was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-458f0fff34824837826df71a51a633b4
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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