m-Chloroperbenzoic acid → HCID 19866665, compound

HRID 232081Notes

Reaction equation

HRID 232081 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[CH:16]=[C:15]([N:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=1[N:20]([CH3:22])[CH3:21].ClC1C=CC=C(C(OO)=[O:31])C=1>C(OCC)(=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([C:11]1[CH:16]=[C:15]([N:17]([CH3:18])[CH3:19])[CH:14]=[CH:13][C:12]=1[N:20]([CH3:22])[CH3:21])=[O:31]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19866626HCID 19866626, compound

Product 1

HCID 19866665HCID 19866665, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The product of step (b) above (1.5 g) was dissolved in ethyl acetate (120 ml) and cooled to -10°. A solution of m-chloroperbenzoic acid (980 mg of 85%) in ethyl acetate (30 ml) was added in one portion and the mixture stirred for 1 hr. The mixture was filtered and the residue taken up in dichloromethane. The dichloromethane was washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine and then dried and evaporated. Flash chromatography afforded the title compound as an off white solid (857 mg) mp 213°-215° NMR (CDCl3) delta 7.7 (broad), 7.4 (2H)broad, 7.20 (2H)m, 7.12 (2H)m, 6.69 (1H)d.o.d., 2.79 (6H) 2.60 (6H)s.

Workup

  1. temperaturecooled to -10°
  2. filtrationThe mixture was filtered
  3. washThe dichloromethane was washed with sodium bicarbonate solution, sodium metabisulphite solution, water and brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-81b69ec5b8a445fda3edea71003b8d42
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Reaction notes

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