m-Chloroperbenzoic acid → HCID 18961892, compound

HRID 1197455Notes

Reaction equation

HRID 1197455 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1)=[O:14].ClC1C=C(C=CC=1)C(OO)=[O:32]>C(Cl)(Cl)Cl.ClCCl>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:23]([F:26])([F:25])[F:24])=[O:32])=[CH:18][CH:17]=1)=[O:14]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 18961896HCID 18961896, compound

Product 1

HCID 18961892HCID 18961892, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent3×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-(3,4-dihydro-4-oxo-3-quinazolinyl)-3-{p-[(trifluoromethyl)thio]phenyl}urea (1.0 g, 2.63 mmol) in chloroform is cooled with an ice-water bath, treated with a solution of 3-chloroperoxybenzoic acid (0.57 g, 80% real, 2.64 mmol) in chloroform, stirred for 3 hours at 0° C., stirred for 32 hours at room temperature, cooled to 0° C., treated with additional 3-chloroperoxybenzoic acid (0.114 g, 0.53 mmol) in chloroform, stirred for 36 hours at room temperature, diluted with dichloromethane, washed sequentially with saturated sodium sulfite solution, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous MgSO4 and concentrated in vacuo to obtain a yellow solid. Chromatography of the solid using silica gel and a 4:1 ethyl acetate/hexanes solution gives the title product as a white solid, 0.50 g, mp 148°-150° C., which is identified by 1HNMR spectral analysis.

Workup

  1. temperatureis cooled with an ice-water bath
  2. stirringstirred for 32 hours at room temperature
  3. temperaturecooled to 0° C.
  4. stirringstirred for 36 hours at room temperature
  5. washwashed sequentially with saturated sodium sulfite solution, saturated sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customto obtain a yellow solid

Sources & evidence

ORD record
ord-d8af8eac6f554f5cb8611b55f641fdbf
Source dataset
uspto-grants-1994_01
Patent number
US05276038

Reaction notes

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