m-Chloroperbenzoic acid → HCID 11763452, compound

HRID 1373722Notes

Reaction equation

HRID 1373722 reaction equation
ClC1C=CC=C(C(OO)=O)C=1.[CH3:12][S:13]([NH:16][CH2:17][CH2:18][NH:19][C:20]([C:22]1[C:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Br:40])=[CH:24][C:25]2[CH:30]=[N:29][C:28](SC)=[N:27][C:26]=2[N:33]=1)=[O:21])(=[O:15])=[O:14].[OH:41][CH2:42][CH2:43][S:44][C:45]1[CH:46]=[C:47]([CH:49]=[CH:50][CH:51]=1)[NH2:48]>ClCCl>[CH3:12][S:13]([NH:16][CH2:17][CH2:18][NH:19][C:20]([C:22]1[C:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Br:40])=[CH:24][C:25]2[CH:30]=[N:29][C:28]([NH:48][C:47]3[CH:49]=[CH:50][CH:51]=[C:45]([S:44][CH2:43][CH2:42][OH:41])[CH:46]=3)=[N:27][C:26]=2[N:33]=1)=[O:21])(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 21075461HCID 21075461, compoundHCID 90962923HCID 90962923, compound

Product 1

HCID 11763452HCID 11763452, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

2.6 g m-chloroperbenzoic acid (MCPBA, purchased from Aldrich, 57–86%) were dissolved in 20 ml dichloromethane and dried by filtration over sodium sulfate. 2 ml of this solution were added at 0–5° C. to a solution of 480 mg (0,97 mmol) of the product from example g in 3 ml dichloromethane. The mixture was allowed to reach RT and monitored by TLC. After 20 min another 0.1 ml of the above MCPBA solution were added at RT and stirring was continued for 10 min. Excess peracid was quenched by addition of 30 μl dimethylsulfide and stirring for another 20 min. The resulting mixture was used immediately without further purification for the next step: 0.625 ml of the above solution (containing 0.12 mmol) were added at RT to a solution of 22 mg meta-(2-hydroxyethylthio)aniline (0.13 mmol) in 0.5 ml dichloromethane. After 15 hrs the mixture was diluted with 10 ml dichloromethane and washed with aqueous acetic acid and with saturated potassium bicarbonate solution. Purification by chromatography on silica yielded 52 mg of the title product.

Workup

  1. dry with materialdried by filtration over sodium sulfate
  2. customto reach RT
  3. customExcess peracid was quenched by addition of 30 μl dimethylsulfide
  4. stirringstirring for another 20 min
  5. customThe resulting mixture was used immediately without further purification for the next step
  6. washwashed with aqueous acetic acid and with saturated potassium bicarbonate solution
  7. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-e57c500c2e7b4403af23a6e22daa8707
Source dataset
uspto-grants-2007_01
Patent number
US07163941B2

Reaction notes

Loading…